The Journal of Organic Chemistry

Dual activation in the esterification of hindered alcohols with anhydrides using MgBr2 and a tertiary amine

E Vedejs, O Daugulis

Index: Vedejs, Edwin; Daugulis, Olafs Journal of Organic Chemistry, 1996 , vol. 61, # 17 p. 5702 - 5703

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Citation Number: 105

Abstract

In the course of studies designed to evaluate reactive acylating agents, we observed that the combination of 2 equiv of MgBr2 (anhydrous solution in THF), 3 equiv of a tertiary amine, and 2 equiv of benzoic anhydride benzoylated the secondary alcohol 1-phenylethanol within seconds (CH2Cl2, exotherm!) Secondary alcohol acylations were not pursued, 1 but we were interested to find that even the hindered pivalic anhydride reacts with alcohols ...