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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 28, 1998 - Issue 11
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Original Articles

Selective Acetylation of Primary Alcohols: Acetyl and Formyl Transfer Reactions with Copper(II) Salts

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Pages 1923-1934 | Received 13 May 1997, Published online: 20 Aug 2006
 

Abstract

The efficient esterification of primary and secondary alcohols in acetic acid was achieved in the presence of Cu(NO3)2.3H2O in high yields. Selective acetylation of primary in the presence of secondary hydroxyl groups in excellent yields were performed in EtOAc. Formylation of primary and secondary alcohols was also achieved easily in ethyl formate. High retention of configuration was observed in the acetylation and formylation of (-) menthol in the presence of Cu(NO3)2. 3H2O and Cu(OAc)2.H2O.

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