392:
to strong acid, in which case other catalytic acids may be chosen. If the product ester has a lower boiling point than either water or the reagents, the product may be distilled rather than water; this is common as esters with no protic functional groups tend to have lower boiling points than their protic parent reagents. Purification and extraction are easier if the ester product can be distilled away from the reagents and byproducts, but reaction rate can be slowed because overall reaction temperature can be limited in this scenario. A more inconvenient scenario is if the reagents have a lower boiling point than either the ester product or water, in which case the reaction mixture must be capped and refluxed and a large excess of starting material added. In this case anhydrous salts, such as
100:
297:
436:—the ester of ethanol and acetic acid—is the most abundant ester in wines. Other combinations of organic alcohols (such as phenol-containing compounds) and organic acids lead to a variety of different esters in wines, contributing to their different flavours, smells and tastes. Of course, when compared to sulfuric acid conditions, the acid conditions in a wine are mild, so yield is low (often in tenths or hundredths of a percentage point by volume) and take years for ester to accumulate.
364:
esterification pathway, but at a much slower pace. However, in many carefully designed syntheses, reagents can be designed such that acid anhydrides are generated in situ and carboxylic acid byproducts are reactivated, and
Fischer esterification routes are not necessarily mutually exclusive with acetic anhydride routes. Examples of this include the common undergraduate organic lab experiment involving the acetylation of
2761:
391:
The primary disadvantages of
Fischer esterification routes are its thermodynamic reversibility and relatively slow reaction rates—often on the scale of several hours to years, depending on the reaction conditions. Workarounds to this can be inconvenient if there are other functional groups sensitive
314:
The primary advantages of
Fischer esterification compared to other esterification processes are based on its relative simplicity. Straightforward acidic conditions can be used if acid-sensitive functional groups are not an issue; sulfuric acid can be used; weaker acids can be used with a tradeoff of
363:
is eliminated as a leaving group, which is considerably less reactive than an acid anhydride and will be left as a byproduct (in a wasteful 1:1 ratio with the ester product) if product is collected immediately. If conditions are acidic enough, the acetic acid can be further reacted via the
Fischer
331:
gas upon contact with atmospheric moisture, are corrosive, react vigorously with water and other nucleophiles (sometimes dangerously); they are easily quenched by other nucleophiles besides the desired alcohol; their most common synthesis routes involve the evolution of toxic
379:: because of its slowness, the most stable ester tends to be the major product. This can be a desirable trait if there are multiple reaction sites and side product esters to be avoided. In contrast, rapid reactions involving acid anhydrides or acid chlorides are often
242:
carbon and the nucleophilicity of an alcohol. Carboxylic acids tend to be deprotonated by nucleophiles, which gives an unreactive carboxylate. Although kinetically very stable in the absence of catalysts, esters tend to eventually hydrolyse in the presence of water.
455:
released by TBATB protonates the alcohol rather than the carboxylic acid, making the carboxylate the actual nucleophile. This would be a reversal of the standard esterification mechanism. An example of this method is the acylation of 3-phenylpropanol using
146:. Contrary to common misconception found in organic chemistry textbooks, phenols can also be esterified to give good to near quantitative yield of products. Commonly used catalysts for a Fischer esterification include
315:
longer reaction times. Because the reagents used are "direct," there is less environmental impact in terms of waste products and harmfulness of the reagents. Alkyl halides are potential
733:
142:
and Arthur Speier in 1895. Most carboxylic acids are suitable for the reaction, but the alcohol should generally be primary or secondary. Tertiary alcohols are prone to
432:
in an aging wine will catalytically protonate other organic acids (including acetic acid itself), encouraging ethanol to react as a nucleophile. As a result,
212:
that must be remedied (e.g. by a large excess of one of the reagents), or by the removal of water (e.g. by using Dean–Stark distillation or including a
347:
anion—a better leaving group than an alkoxide anion because their negative charge is more delocalised. However, such routes generally result in poor
173:
are used. The reaction is often carried out without a solvent (particularly when a large reagent excess of the alcohol reagent is used) or in a
296:
668:
86:
709:
424:
and other alcoholic beverages during the aging process is an example of acid-catalysed esterification. Over time, the acidity of the
2795:
2512:
608:
555:
Hocking, M.B. (1980). "Phenyl acetate preparation from phenol and acetic acid: Reassessment of a common textbook misconception".
2790:
2741:
2607:
1701:
1644:
444:
186:
2785:
1007:
879:
2717:
2016:
947:
942:
79:
99:
2736:
2727:
2707:
937:
600:
2815:
2810:
2061:
71:
189:
to remove the water byproduct. Typical reaction times vary from 1–10 hours at temperatures of 60–110 °C.
2800:
2592:
1958:
170:
404:, shifting the equilibrium towards ester products. The reaction mixture containing the product can then be
2597:
1424:
1414:
1409:
982:
932:
927:
702:
162:
151:
2123:
1666:
1434:
1429:
1419:
1352:
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1336:
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2021:
1681:
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1404:
1394:
1362:
1357:
1347:
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2108:
1559:
1399:
1331:
1320:
594:
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1389:
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564:
529:
209:
143:
2362:
2103:
1265:
2746:
2098:
2041:
2003:
1676:
1661:
1639:
987:
899:
799:
718:
457:
131:
45:
2367:
2357:
1254:
2660:
2641:
2517:
2133:
1978:
1973:
1968:
1963:
1718:
1584:
1050:
889:
781:
748:
409:
393:
250:
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2616:
2128:
1731:
1710:
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1634:
1629:
1532:
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1502:
1492:
1487:
972:
904:
840:
773:
768:
695:
628:
604:
328:
55:
238:
Fischer esterification is an acyl substitution reaction based on the electrophilicity of the
2165:
2113:
2056:
1883:
1830:
1726:
1624:
1527:
1497:
1477:
1467:
1325:
977:
572:
537:
502:
452:
352:
208:(moisture sensitive reagents). The main disadvantage of direct acylation is the unfavorable
682:
2700:
2669:
2602:
2569:
2522:
2507:
2175:
1869:
1864:
1825:
1549:
1517:
1482:
1032:
967:
962:
957:
952:
894:
859:
758:
380:
333:
320:
282:
Protonation of one of the hydroxy groups of the activated complex gives a new oxonium ion.
221:
127:
104:
568:
533:
2731:
2646:
2502:
2051:
2011:
1696:
1472:
1462:
1457:
1447:
1314:
1276:
1259:
1243:
1199:
1188:
1182:
1027:
922:
812:
461:
365:
337:
316:
233:
119:
17:
2779:
2685:
2584:
2143:
2118:
2090:
2033:
1856:
1804:
1691:
1619:
1614:
1452:
1287:
1281:
1270:
1210:
1204:
1193:
884:
832:
807:
658:
Tetrabutylammonium tribromide mediated condensation of carboxylic acids with alcohols
433:
429:
356:
246:
Several steps can be taken to turn this unfavourable reaction into a favourable one.
205:
147:
135:
2574:
1950:
1609:
1177:
1002:
348:
262:
201:
166:
139:
41:
2690:
2554:
2401:
1993:
1988:
1983:
1774:
1248:
1171:
1165:
425:
360:
344:
276:
269:
2651:
2636:
2564:
2559:
2464:
2265:
2195:
2071:
1893:
1794:
1604:
1599:
1569:
1564:
1522:
1237:
1120:
1110:
1100:
1055:
789:
763:
743:
506:
324:
158:
343:
Acid anhydrides are more reactive than esters because the leaving group is a
2459:
2449:
2431:
2285:
2076:
1931:
1784:
1594:
1589:
1579:
1574:
1554:
1159:
1131:
1125:
1115:
1105:
1060:
217:
213:
197:
193:
285:
Loss of water from this oxonium ion and subsequent deprotonation gives the
224:, or a large amount of certain acids as catalyst in the reaction mixture).
593:
Furniss, Brian; Hannaford, Antony; Smith, Peter; Tatchell, Austin (1996).
2538:
2454:
2426:
2411:
2406:
2347:
2342:
2326:
2255:
2245:
2215:
2205:
2185:
1921:
1917:
1897:
1879:
1846:
1754:
1090:
871:
845:
448:
405:
258:
239:
2655:
2416:
2396:
2352:
2308:
2235:
2225:
2066:
2046:
1907:
1764:
1095:
1042:
997:
914:
820:
753:
661:
660:
Sarala Naik, Veerababurao Kavala, Rangam
Gopinath, and Bhisma K. Patel
401:
369:
293:
A generic mechanism for an acid
Fischer esterification is shown below.
178:
174:
576:
520:
Offenhauer, Robert D. (1964). "The direct esterification of phenols".
2664:
2482:
2275:
1507:
541:
182:
123:
196:
of alcohols with carboxylic acids is preferred over acylations with
460:
and TBATB. The reaction generates the ester in 15 minutes in a 95%
2421:
286:
98:
421:
691:
279:
to a second molecule of the alcohol gives an activated complex
493:
Emil
Fischer, Arthur Speier (1895). "Darstellung der Ester".
295:
687:
408:
or filtered to remove the drying agent prior to the final
165:. For more valuable or sensitive substrates (for example,
327:, and possible ecological poisons. Acid chlorides evolve
596:
Vogel's
Textbook of Practical Organic Chemistry 5th Ed
400:, can also be added to sequester the water by forming
447:(TBATB) can serve as an effective but unconventional
599:. London: Longman Science & Technical. pp.
2678:
2625:
2583:
2547:
2531:
2495:
2473:
2440:
2387:
2380:
2335:
2317:
2299:
2151:
2142:
2085:
2030:
2002:
1949:
1855:
1839:
1818:
1747:
1740:
1652:
1541:
1371:
1296:
1219:
1141:
1072:
1041:
913:
870:
858:
831:
798:
732:
725:
340:gases (depending on the synthesis process used).
420:The natural esterification that takes place in
703:
8:
268:The carbonyl carbon is then attacked by the
2384:
2148:
1744:
867:
729:
710:
696:
688:
29:
476:- the coupling of an alcohol and a sugar
351:. For example, in reacting ethanol with
622:
620:
588:
586:
485:
451:for this reaction. It is believed that
375:Fischer esterification is primarily a
257:Proton transfer from acid catalyst to
138:. The reaction was first described by
253:for this reaction has several steps:
7:
1857:Polyhydric alcohols (sugar alcohols)
377:thermodynamically-controlled process
683:Animation of Fischer esterification
169:) other, milder procedures such as
464:without the need to remove water.
25:
2513:2-Methyl-2-propyl-1,3-propanediol
2760:
2759:
300:Fischer esterification mechanism
107:by Fischer–Speier esterification
2742:Nucleophilic conjugate addition
1:
2713:Fischer–Speier esterification
1645:Propylene glycol methyl ether
557:Journal of Chemical Education
522:Journal of Chemical Education
445:Tetrabutylammonium tribromide
116:Fischer–Speier esterification
305:Advantages and disadvantages
880:4-Methylcyclohexanemethanol
2832:
2718:Williamson ether synthesis
2017:2,4-Dichlorobenzyl alcohol
948:2-(2-Methoxyethoxy)ethanol
943:2-(2-Methoxyethoxy)ethanol
627:Tingle, J. Bishop (1906).
272:oxygen atom of the alcohol
231:
2755:
2737:Friedel-Crafts alkylation
2728:Nucleophilic substitution
2708:Nucleophilic substitution
938:2-(2-Ethoxyethoxy)ethanol
633:American Chemical Journal
629:"Reports: Esterification"
507:10.1002/cber.189502803176
275:Proton transfer from the
93:
67:Organic Chemistry Portal
61:
32:
27:Type of chemical reaction
2796:Esterification reactions
1959:2,2-Dimethylpropan-1-ol
1015:-Diisopropylaminoethanol
2593:1,3-Difluoro-2-propanol
187:Dean–Stark distillation
171:Steglich esterification
2791:Condensation reactions
2598:2,2,2-Trifluoroethanol
983:Aminoethylethanolamine
933:2,2,2-Trifluoroethanol
928:2,2,2-Trichloroethanol
381:kinetically-controlled
301:
185:) that can facilitate
163:scandium(III) triflate
134:in the presence of an
112:Fischer esterification
108:
72:fischer-esterification
18:Fischer esterification
2022:3-Nitrobenzyl alcohol
474:Fischer glycosidation
398:potassium pyrosulfate
299:
155:-toluenesulfonic acid
118:is a special type of
102:
2723:Elimination reaction
1425:1-Heptatetracontanol
1415:1-Pentatetracontanol
1410:1-Tetratetracontanol
1317:(melissyl / myricyl)
1284:(cluytyl / montanyl)
993:Dimethylethanolamine
603:–697 & 699–704.
210:chemical equilibrium
204:of the reaction) or
2747:Transesterification
2124:Palmitoleyl alcohol
2099:3-Methyl-3-pentanol
2042:Cetostearyl alcohol
1979:3-Methylbutan-2-ol
1974:3-Methylbutan-1-ol
1969:2-Methylbutan-2-ol
1964:2-Methylbutan-1-ol
1748:Monohydric alcohols
1677:3-Methyl-3-pentanol
1667:2-Methylheptan-2-ol
1662:2-Methyl-2-pentanol
1435:1-Nonatetracontanol
1430:1-Octatetracontanol
1420:1-Hexatetracontanol
1353:1-Heptatriacontanol
1343:1-Pentatriacontanol
1337:1-Tetratriacontanol
1023:-Methylethanolamine
988:Diethylethanolamine
900:Methylazoxymethanol
817:Methanol poisoning
569:1980JChEd..57..527H
534:1964JChEd..41...39O
458:glacial acetic acid
265:of carbonyl carbon.
2786:Coupling reactions
2642:Carbonyl reduction
2518:Diethylpropanediol
2134:tert-Butyl alcohol
1840:Trihydric alcohols
1682:3-Methyloctan-3-ol
1672:2-Methylhexan-2-ol
1585:3-Methyl-2-butanol
1405:1-Tritetracontanol
1395:1-Hentetracontanol
1363:1-Nonatriacontanol
1358:1-Octatriacontanol
1348:1-Hexatriacontanol
1196:(cetyl / palmityl)
1051:2-Methyl-1-butanol
890:Cyclohexylmethanol
749:2-Methyl-1-butanol
495:Chemische Berichte
394:copper(II) sulfate
302:
251:reaction mechanism
109:
2773:
2772:
2696:Alcohol oxidation
2617:Trifluoromethanol
2491:
2490:
2376:
2375:
2129:tert-Amyl alcohol
2109:Linolenyl alcohol
2004:Aromatic alcohols
1945:
1944:
1819:Dihydric alcohols
1732:Triphenylmethanol
1687:Diacetone alcohol
1635:Pinacolyl alcohol
1560:2-Deoxyerythritol
1533:Veratrole alcohol
1513:Propargyl alcohol
1503:Phenethyl alcohol
1493:Nicotinyl alcohol
1488:Neopentyl alcohol
1443:
1442:
1400:1-Dotetracontanol
1332:1-Tritriacontanol
1321:1-Hentriacontanol
973:2-Mercaptoethanol
905:Trifluoromethanol
854:
853:
841:Isopropyl alcohol
769:Phenethyl alcohol
734:Alcohols found in
577:10.1021/ed057p527
329:hydrogen chloride
261:oxygen increases
175:non-polar solvent
103:The synthesis of
97:
96:
56:Coupling reaction
16:(Redirected from
2823:
2763:
2762:
2385:
2381:Terpene alcohols
2166:Methylene glycol
2149:
2114:Linoleyl alcohol
2057:Myristyl alcohol
1884:Propylene glycol
1831:Propylene glycol
1745:
1727:Triphenylethanol
1640:Pirkle's alcohol
1625:Diphenylmethanol
1528:Vanillyl alcohol
1498:Perillyl alcohol
1478:Furfuryl alcohol
1468:Cinnamyl alcohol
1326:1-Dotriacontanol
978:2-Methoxyethanol
868:
736:alcoholic drinks
730:
712:
705:
698:
689:
671:
655:
649:
648:
646:
644:
624:
615:
614:
590:
581:
580:
552:
546:
545:
542:10.1021/ed041p39
517:
511:
510:
501:(3): 3252–3258.
490:
453:hydrobromic acid
353:acetic anhydride
317:greenhouse gases
263:electrophilicity
222:molecular sieves
89:
74:
30:
21:
2831:
2830:
2826:
2825:
2824:
2822:
2821:
2820:
2816:1895 in Germany
2811:1895 in science
2776:
2775:
2774:
2769:
2751:
2701:Glycol cleavage
2674:
2670:Ziegler process
2621:
2603:2-Fluoroethanol
2579:
2543:
2527:
2523:Ethylene glycol
2508:1,5-Pentanediol
2487:
2475:
2469:
2442:
2436:
2389:
2372:
2336:Glycylglycitols
2331:
2319:
2313:
2301:
2295:
2291:
2281:
2271:
2261:
2251:
2241:
2231:
2221:
2211:
2201:
2191:
2181:
2176:Ethylene glycol
2171:
2159:
2155:
2138:
2089:
2087:
2081:
2032:
2026:
1998:
1941:
1937:
1927:
1913:
1903:
1889:
1875:
1870:Ethylene glycol
1865:Pentaerythritol
1851:
1835:
1826:Ethylene glycol
1814:
1810:
1800:
1790:
1780:
1770:
1760:
1741:Hydric alcohols
1736:
1654:
1648:
1550:1-Phenylethanol
1543:
1537:
1518:Salicyl alcohol
1483:Isoamyl alcohol
1439:
1390:1-Tetracontanol
1383:
1379:
1375:
1373:
1367:
1308:
1304:
1300:
1298:
1292:
1231:
1227:
1223:
1221:
1215:
1153:
1149:
1145:
1143:
1137:
1084:
1080:
1076:
1074:
1068:
1037:
1033:Tribromoethanol
968:2-Fluoroethanol
963:2-Ethoxyethanol
958:2-Chloroethanol
953:2-Butoxyethanol
909:
895:Methoxymethanol
861:
850:
827:
800:Medical alcohol
794:
759:Isoamyl alcohol
735:
721:
716:
679:
674:
656:
652:
642:
640:
626:
625:
618:
611:
592:
591:
584:
554:
553:
549:
519:
518:
514:
492:
491:
487:
483:
470:
442:
418:
389:
334:carbon monoxide
321:ozone depletors
312:
307:
236:
230:
128:carboxylic acid
105:methyl benzoate
85:
70:
44:
33:Esterification
28:
23:
22:
15:
12:
11:
5:
2829:
2827:
2819:
2818:
2813:
2808:
2803:
2801:Name reactions
2798:
2793:
2788:
2778:
2777:
2771:
2770:
2768:
2767:
2756:
2753:
2752:
2750:
2749:
2744:
2739:
2734:
2732:carbonyl group
2725:
2720:
2715:
2710:
2705:
2704:
2703:
2693:
2688:
2682:
2680:
2676:
2675:
2673:
2672:
2667:
2658:
2649:
2647:Ether cleavage
2644:
2639:
2629:
2627:
2623:
2622:
2620:
2619:
2614:
2612:-butyl alcohol
2605:
2600:
2595:
2589:
2587:
2585:Fluoroalcohols
2581:
2580:
2578:
2577:
2572:
2567:
2562:
2557:
2551:
2549:
2545:
2544:
2542:
2541:
2535:
2533:
2529:
2528:
2526:
2525:
2520:
2515:
2510:
2505:
2503:1,4-Butanediol
2499:
2497:
2493:
2492:
2489:
2488:
2486:
2485:
2479:
2477:
2471:
2470:
2468:
2467:
2462:
2457:
2452:
2446:
2444:
2438:
2437:
2435:
2434:
2429:
2424:
2419:
2414:
2409:
2404:
2399:
2393:
2391:
2382:
2378:
2377:
2374:
2373:
2371:
2370:
2365:
2363:Maltotetraitol
2360:
2355:
2350:
2345:
2339:
2337:
2333:
2332:
2330:
2329:
2323:
2321:
2315:
2314:
2312:
2311:
2305:
2303:
2297:
2296:
2294:
2293:
2289:
2283:
2279:
2273:
2269:
2263:
2259:
2253:
2249:
2243:
2239:
2233:
2229:
2223:
2219:
2213:
2209:
2203:
2199:
2193:
2189:
2183:
2179:
2173:
2169:
2162:
2160:
2157:
2153:
2146:
2144:Sugar alcohols
2140:
2139:
2137:
2136:
2131:
2126:
2121:
2116:
2111:
2106:
2104:Erucyl alcohol
2101:
2095:
2093:
2091:fatty alcohols
2083:
2082:
2080:
2079:
2074:
2069:
2064:
2059:
2054:
2052:Lauryl alcohol
2049:
2044:
2038:
2036:
2034:fatty alcohols
2028:
2027:
2025:
2024:
2019:
2014:
2012:Benzyl alcohol
2008:
2006:
2000:
1999:
1997:
1996:
1991:
1986:
1981:
1976:
1971:
1966:
1961:
1955:
1953:
1947:
1946:
1943:
1942:
1940:
1939:
1935:
1929:
1925:
1915:
1911:
1905:
1901:
1891:
1887:
1877:
1873:
1867:
1861:
1859:
1853:
1852:
1850:
1849:
1843:
1841:
1837:
1836:
1834:
1833:
1828:
1822:
1820:
1816:
1815:
1813:
1812:
1808:
1802:
1798:
1792:
1788:
1782:
1778:
1772:
1768:
1762:
1758:
1751:
1749:
1742:
1738:
1737:
1735:
1734:
1729:
1724:
1722:-Butyl alcohol
1716:
1708:
1706:-butyl alcohol
1699:
1697:Methylpentynol
1694:
1689:
1684:
1679:
1674:
1669:
1664:
1658:
1656:
1650:
1649:
1647:
1642:
1637:
1632:
1627:
1622:
1617:
1612:
1607:
1602:
1597:
1592:
1587:
1582:
1577:
1572:
1567:
1562:
1557:
1552:
1547:
1545:
1539:
1538:
1536:
1535:
1530:
1525:
1520:
1515:
1510:
1505:
1500:
1495:
1490:
1485:
1480:
1475:
1473:Crotyl alcohol
1470:
1465:
1463:Benzyl alcohol
1460:
1458:Anisyl alcohol
1455:
1450:
1448:2-Ethylhexanol
1444:
1441:
1440:
1438:
1437:
1432:
1427:
1422:
1417:
1412:
1407:
1402:
1397:
1392:
1386:
1384:
1381:
1377:
1372:Straight-chain
1369:
1368:
1366:
1365:
1360:
1355:
1350:
1345:
1340:
1334:
1329:
1323:
1318:
1315:1-Triacontanol
1311:
1309:
1306:
1302:
1297:Straight-chain
1294:
1293:
1291:
1290:
1285:
1279:
1277:1-Heptacosanol
1274:
1268:
1266:1-Pentacosanol
1263:
1260:1-Tetracosanol
1257:
1252:
1246:
1244:1-Heneicosanol
1241:
1234:
1232:
1229:
1225:
1220:Straight-chain
1217:
1216:
1214:
1213:
1208:
1202:
1200:1-Heptadecanol
1197:
1191:
1189:1-Pentadecanol
1186:
1183:1-Tetradecanol
1180:
1175:
1169:
1163:
1156:
1154:
1151:
1147:
1142:Straight-chain
1139:
1138:
1136:
1135:
1129:
1123:
1118:
1113:
1108:
1103:
1098:
1093:
1087:
1085:
1082:
1078:
1073:Straight-chain
1070:
1069:
1067:
1066:
1058:
1053:
1047:
1045:
1039:
1038:
1036:
1035:
1030:
1028:Phenoxyethanol
1025:
1017:
1005:
1000:
995:
990:
985:
980:
975:
970:
965:
960:
955:
950:
945:
940:
935:
930:
925:
923:1-Aminoethanol
919:
917:
911:
910:
908:
907:
902:
897:
892:
887:
882:
876:
874:
865:
856:
855:
852:
851:
849:
848:
843:
837:
835:
833:Toxic alcohols
829:
828:
826:
825:
824:
823:
815:
813:Methylpentynol
810:
804:
802:
796:
795:
793:
792:
787:
785:-Butyl alcohol
779:
771:
766:
761:
756:
751:
746:
740:
738:
727:
726:By consumption
723:
722:
717:
715:
714:
707:
700:
692:
686:
685:
678:
677:External links
675:
673:
672:
669:Online Article
650:
616:
609:
582:
547:
512:
484:
482:
479:
478:
477:
469:
466:
441:
438:
417:
414:
388:
385:
366:salicylic acid
338:sulfur dioxide
311:
308:
306:
303:
291:
290:
283:
280:
273:
266:
234:Esterification
232:Main article:
229:
226:
206:acid chlorides
120:esterification
95:
94:
91:
90:
83:
76:
75:
68:
64:
63:
59:
58:
53:
52:Reaction type
49:
48:
39:
35:
34:
26:
24:
14:
13:
10:
9:
6:
4:
3:
2:
2828:
2817:
2814:
2812:
2809:
2807:
2804:
2802:
2799:
2797:
2794:
2792:
2789:
2787:
2784:
2783:
2781:
2766:
2758:
2757:
2754:
2748:
2745:
2743:
2740:
2738:
2735:
2733:
2729:
2726:
2724:
2721:
2719:
2716:
2714:
2711:
2709:
2706:
2702:
2699:
2698:
2697:
2694:
2692:
2689:
2687:
2686:Deprotonation
2684:
2683:
2681:
2677:
2671:
2668:
2666:
2662:
2659:
2657:
2653:
2650:
2648:
2645:
2643:
2640:
2638:
2634:
2631:
2630:
2628:
2624:
2618:
2615:
2613:
2611:
2606:
2604:
2601:
2599:
2596:
2594:
2591:
2590:
2588:
2586:
2582:
2576:
2573:
2571:
2568:
2566:
2563:
2561:
2558:
2556:
2553:
2552:
2550:
2546:
2540:
2537:
2536:
2534:
2530:
2524:
2521:
2519:
2516:
2514:
2511:
2509:
2506:
2504:
2501:
2500:
2498:
2494:
2484:
2481:
2480:
2478:
2472:
2466:
2463:
2461:
2458:
2456:
2453:
2451:
2448:
2447:
2445:
2441:Sesquiterpene
2439:
2433:
2430:
2428:
2425:
2423:
2420:
2418:
2415:
2413:
2410:
2408:
2405:
2403:
2400:
2398:
2395:
2394:
2392:
2386:
2383:
2379:
2369:
2366:
2364:
2361:
2359:
2356:
2354:
2351:
2349:
2346:
2344:
2341:
2340:
2338:
2334:
2328:
2325:
2324:
2322:
2316:
2310:
2307:
2306:
2304:
2298:
2287:
2284:
2277:
2274:
2267:
2264:
2257:
2254:
2247:
2244:
2237:
2234:
2227:
2224:
2217:
2214:
2207:
2204:
2197:
2194:
2187:
2184:
2177:
2174:
2167:
2164:
2163:
2161:
2150:
2147:
2145:
2141:
2135:
2132:
2130:
2127:
2125:
2122:
2120:
2119:Oleyl alcohol
2117:
2115:
2112:
2110:
2107:
2105:
2102:
2100:
2097:
2096:
2094:
2092:
2084:
2078:
2075:
2073:
2070:
2068:
2065:
2063:
2060:
2058:
2055:
2053:
2050:
2048:
2045:
2043:
2040:
2039:
2037:
2035:
2029:
2023:
2020:
2018:
2015:
2013:
2010:
2009:
2007:
2005:
2001:
1995:
1992:
1990:
1987:
1985:
1982:
1980:
1977:
1975:
1972:
1970:
1967:
1965:
1962:
1960:
1957:
1956:
1954:
1952:
1951:Amyl alcohols
1948:
1933:
1930:
1923:
1919:
1916:
1909:
1906:
1899:
1895:
1892:
1885:
1881:
1878:
1871:
1868:
1866:
1863:
1862:
1860:
1858:
1854:
1848:
1845:
1844:
1842:
1838:
1832:
1829:
1827:
1824:
1823:
1821:
1817:
1806:
1805:Cetyl alcohol
1803:
1796:
1793:
1786:
1783:
1776:
1773:
1766:
1763:
1756:
1753:
1752:
1750:
1746:
1743:
1739:
1733:
1730:
1728:
1725:
1723:
1721:
1717:
1715:
1714:-Amyl alcohol
1713:
1709:
1707:
1705:
1700:
1698:
1695:
1693:
1692:Ethchlorvynol
1690:
1688:
1685:
1683:
1680:
1678:
1675:
1673:
1670:
1668:
1665:
1663:
1660:
1659:
1657:
1655:alcohols (3°)
1651:
1646:
1643:
1641:
1638:
1636:
1633:
1631:
1628:
1626:
1623:
1621:
1620:Cyclopropanol
1618:
1616:
1615:Cyclopentanol
1613:
1611:
1608:
1606:
1603:
1601:
1598:
1596:
1593:
1591:
1588:
1586:
1583:
1581:
1578:
1576:
1573:
1571:
1568:
1566:
1563:
1561:
1558:
1556:
1553:
1551:
1548:
1546:
1544:alcohols (2°)
1540:
1534:
1531:
1529:
1526:
1524:
1521:
1519:
1516:
1514:
1511:
1509:
1506:
1504:
1501:
1499:
1496:
1494:
1491:
1489:
1486:
1484:
1481:
1479:
1476:
1474:
1471:
1469:
1466:
1464:
1461:
1459:
1456:
1454:
1453:Allyl alcohol
1451:
1449:
1446:
1445:
1436:
1433:
1431:
1428:
1426:
1423:
1421:
1418:
1416:
1413:
1411:
1408:
1406:
1403:
1401:
1398:
1396:
1393:
1391:
1388:
1387:
1385:
1370:
1364:
1361:
1359:
1356:
1354:
1351:
1349:
1346:
1344:
1341:
1338:
1335:
1333:
1330:
1327:
1324:
1322:
1319:
1316:
1313:
1312:
1310:
1295:
1289:
1288:1-Nonacosanol
1286:
1283:
1282:1-Octacosanol
1280:
1278:
1275:
1272:
1271:1-Hexacosanol
1269:
1267:
1264:
1261:
1258:
1256:
1253:
1250:
1247:
1245:
1242:
1239:
1236:
1235:
1233:
1218:
1212:
1211:1-Nonadecanol
1209:
1206:
1205:1-Octadecanol
1203:
1201:
1198:
1195:
1194:1-Hexadecanol
1192:
1190:
1187:
1184:
1181:
1179:
1176:
1173:
1170:
1167:
1164:
1161:
1158:
1157:
1155:
1140:
1133:
1130:
1127:
1124:
1122:
1119:
1117:
1114:
1112:
1109:
1107:
1104:
1102:
1099:
1097:
1094:
1092:
1089:
1088:
1086:
1071:
1065:
1063:
1059:
1057:
1054:
1052:
1049:
1048:
1046:
1044:
1040:
1034:
1031:
1029:
1026:
1024:
1022:
1018:
1016:
1014:
1010:
1006:
1004:
1001:
999:
996:
994:
991:
989:
986:
984:
981:
979:
976:
974:
971:
969:
966:
964:
961:
959:
956:
954:
951:
949:
946:
944:
941:
939:
936:
934:
931:
929:
926:
924:
921:
920:
918:
916:
912:
906:
903:
901:
898:
896:
893:
891:
888:
886:
885:Aminomethanol
883:
881:
878:
877:
875:
873:
869:
866:
863:
857:
847:
844:
842:
839:
838:
836:
834:
830:
822:
819:
818:
816:
814:
811:
809:
808:Ethchlorvynol
806:
805:
803:
801:
797:
791:
788:
786:
784:
780:
778:
777:-Amyl alcohol
776:
772:
770:
767:
765:
762:
760:
757:
755:
752:
750:
747:
745:
742:
741:
739:
737:
731:
728:
724:
720:
713:
708:
706:
701:
699:
694:
693:
690:
684:
681:
680:
676:
670:
666:
663:
659:
654:
651:
638:
634:
630:
623:
621:
617:
612:
610:9780582462366
606:
602:
598:
597:
589:
587:
583:
578:
574:
570:
566:
562:
558:
551:
548:
543:
539:
535:
531:
527:
523:
516:
513:
508:
504:
500:
496:
489:
486:
480:
475:
472:
471:
467:
465:
463:
459:
454:
450:
446:
439:
437:
435:
434:ethyl acetate
431:
427:
423:
416:In wine aging
415:
413:
411:
407:
403:
399:
395:
387:Disadvantages
386:
384:
382:
378:
373:
371:
367:
362:
358:
357:ethyl acetate
354:
350:
346:
341:
339:
335:
330:
326:
322:
318:
309:
304:
298:
294:
288:
284:
281:
278:
274:
271:
267:
264:
260:
256:
255:
254:
252:
247:
244:
241:
235:
227:
225:
223:
219:
215:
211:
207:
203:
199:
195:
190:
188:
184:
180:
176:
172:
168:
164:
160:
156:
154:
149:
148:sulfuric acid
145:
141:
137:
136:acid catalyst
133:
129:
125:
121:
117:
113:
106:
101:
92:
88:
84:
81:
78:
77:
73:
69:
66:
65:
60:
57:
54:
51:
50:
47:
46:Arthur Speier
43:
40:
37:
36:
31:
19:
2806:Emil Fischer
2712:
2633:Substitution
2626:Preparations
2609:
2575:Stigmasterol
2570:β-Sitosterol
2368:Polyglycitol
2358:Maltotriitol
2318:Cyclic sugar
2086:Branched and
1994:Pentan-3-ol
1989:Pentan-2-ol
1984:Pentan-1-ol
1719:
1711:
1703:
1610:Cyclohexanol
1262:(lignoceryl)
1255:1-Tricosanol
1178:1-Tridecanol
1134:(pelargonic)
1061:
1020:
1012:
1008:
1003:Ethanolamine
782:
774:
667:(i) 119-127
664:
657:
653:
641:. Retrieved
636:
632:
595:
560:
556:
550:
525:
521:
515:
498:
494:
488:
443:
419:
390:
374:
349:atom economy
342:
313:
292:
270:nucleophilic
248:
245:
237:
214:drying agent
202:atom economy
191:
167:biomaterials
152:
140:Emil Fischer
115:
111:
110:
87:RXNO:0000167
82:ontology ID
62:Identifiers
42:Emil Fischer
38:Named after
2691:Protonation
2608:Nonafluoro-
2555:Cholesterol
2532:Trialcohols
2402:Citronellol
2388:Monoterpene
2300:Deoxy sugar
2088:unsaturated
1775:Isopropanol
1702:Nonafluoro-
1630:Isopropanol
1249:1-Docosanol
1240:(arachidyl)
1172:1-Dodecanol
1166:1-Undecanol
426:acetic acid
361:acetic acid
345:carboxylate
325:carcinogens
277:oxonium ion
159:Lewis acids
144:elimination
2780:Categories
2652:Hydrolysis
2637:haloalkane
2565:Lanosterol
2560:Ergosterol
2496:Dialcohols
2465:Patchoulol
2266:Galactitol
2196:Erythritol
2072:Tridecanol
1894:Erythritol
1795:1-Pentanol
1605:3-Pentanol
1600:2-Pentanol
1570:3-Heptanol
1565:2-Heptanol
1523:Tryptophol
1328:(lacceryl)
1238:1-Icosanol
1185:(myristyl)
1168:(hendecyl)
1121:1-Heptanol
1111:1-Pentanol
1101:1-Propanol
1056:Isobutanol
790:Tryptophol
764:Isobutanol
744:1-Propanol
643:19 January
563:(7): 527.
481:References
440:Variations
359:forms and
310:Advantages
198:anhydrides
194:acylations
2679:Reactions
2661:Hydration
2474:Diterpene
2460:Nerolidol
2450:Bisabolol
2432:Terpineol
2286:Volemitol
2077:Undecanol
2031:Saturated
1932:Volemitol
1785:1-Butanol
1595:2-Octanol
1590:2-Nonanol
1580:3-Hexanol
1575:2-Hexanol
1555:2-Butanol
1542:Secondary
1374:saturated
1299:saturated
1251:(behenyl)
1222:saturated
1207:(stearyl)
1160:1-Decanol
1144:saturated
1132:1-Nonanol
1126:1-Octanol
1116:1-Hexanol
1106:1-Butanol
1075:saturated
639:: 368–369
528:(1): 39.
368:to yield
218:anhydrous
124:refluxing
2765:Category
2539:Glycerol
2476:alcohols
2455:Farnesol
2443:alcohols
2427:Rhodinol
2412:Linalool
2407:Geraniol
2390:alcohols
2348:Lactitol
2343:Maltitol
2327:Inositol
2320:alcohols
2302:alcohols
2256:Sorbitol
2246:Mannitol
2216:Arabitol
2206:Threitol
2186:Glycerol
1922:Sorbitol
1918:Mannitol
1898:Threitol
1880:Glycerol
1847:Glycerol
1755:Methanol
1653:Tertiary
1339:(geddyl)
1174:(lauryl)
1162:(capric)
1128:(capryl)
1091:Methanol
1064:-Butanol
872:Methanol
862:alcohols
846:Methanol
719:Alcohols
468:See also
449:catalyst
406:decanted
402:hydrates
259:carbonyl
240:carbonyl
228:Overview
216:such as
161:such as
2656:epoxide
2548:Sterols
2417:Menthol
2397:Borneol
2353:Isomalt
2309:Fucitol
2236:Xylitol
2226:Ribitol
2067:Octanol
2062:Nonanol
2047:Decanol
1908:Xylitol
1765:Ethanol
1273:(ceryl)
1096:Ethanol
1043:Butanol
998:Ethanol
915:Ethanol
860:Primary
821:Ethanol
754:Ethanol
662:Arkivoc
565:Bibcode
530:Bibcode
430:tannins
370:aspirin
220:salts,
192:Direct
179:toluene
132:alcohol
130:and an
2665:alkene
2483:Phytol
2276:Iditol
1508:Prenol
607:
410:workup
200:(poor
183:hexane
177:(e.g.
157:, and
2422:Nerol
462:yield
422:wines
287:ester
2610:tert
1720:tert
1712:tert
1704:tert
864:(1°)
783:tert
775:tert
665:2006
645:2016
605:ISBN
428:and
249:The
2730:of
2663:of
2654:of
2635:of
2156:— C
1380:— C
1305:— C
1228:— C
1150:— C
1081:— C
601:695
573:doi
538:doi
503:doi
396:or
336:or
319:or
122:by
114:or
80:RSC
2782::
2288:(C
2278:(C
2268:(C
2258:(C
2248:(C
2238:(C
2228:(C
2218:(C
2208:(C
2198:(C
2188:(C
2178:(C
2168:(C
1934:(C
1924:(C
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