Influence of carboxylic acids on the synthesis of chlorohydrin esters from 1,3-butanediol

被引：8
|
作者：
Méndez, J
Eras, J
Balcells, M
Canela, R
机构：
[1] Univ Lleida, Dept Quim, Lleida 25198, Spain
[2] Univ Lleida, Ctr Udl, IRTA, Lleida 25198, Spain
来源：
SYNTHETIC COMMUNICATIONS | 2006年 / 36卷 / 09期
关键词：
carboxylic acids; chlorohydrin esters; chlorotrimethylsilane; diol; halogenation; regioselectivity;
D O I：
10.1080/00397910500514055
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The influence of diverse carboxylic acid on the preparation of chlorohydrin esters using a one-pot esterification-chlorination reaction, in which one of the reagents (chlorotrimethylsilane) acts as solvent, is described. Whereas the acid with low pKa provided higher amounts of the 2-chloro regioisomer, the ones with higher pKa rendered the 1-chloro regioisomer in 80% yield. These results are in accordance with the mechanism proposed in a previous article.
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页码：1167 / 1175
页数：9
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