Convenient Esterification of Carboxylic Acids by SN2 Reaction Promoted by a Protic Ionic-Liquid System Formed in Situ in Solvent-Free Conditions

被引：27

作者：

Cardellini, Fabio ^{[1
]}

Brinchi, Lucia ^{[1
]}

Germani, Raimondo ^{[1
]}

Tiecco, Matteo ^{[1
]}

机构：

[1] Univ Perugia, Dept Chem Biol & Biotechnol, CEMIN, I-06123 Perugia, Italy

来源：

SYNTHETIC COMMUNICATIONS | 2014年 / 44卷 / 22期

关键词：

nucleophilic substitution; methanesulfonate anion; triethylamine; protic ionic liquids; Esterification; solvent-free reaction; REACTION MEDIA; HALIDES; ESTERS; FACILE;

D O I：

10.1080/00397911.2014.933353

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of esterification of benzoic acid with benzyl chloride was chosen as a model reaction to study the esterification by S(N)2 promoted by tertiary amine as deprotonating agent. The use of ionic liquid (IL) 1,3-dimethylimidazolium methanesulfonate [MMIm][OMs] as reaction medium has proven to give quantitative yield of the ester, but interestingly the reaction does occur even in solvent-free conditions, where the acid + the amine form a liquid system (a protic IL) in situ. This last methodology was extended to several carboxylic acids in conditions of atom economy (i.e., without excess of any reagent), giving moderately good yields of esters (54-78%) recovered by weight in pure form.

引用

页码：3248 / 3256

页数：9

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