Facile and efficient acetylation of primary alcohols and phenols with acetic anhydride catalyzed by dried sodium bicarbonate

Abstract

A variety of primary alcohols and phenols were reacted with acetic anhydride at room temperature in the presence of sodium bicarbonate to produce corresponding esters in good to excellent yields. The acetylation of 4-nitrobenzyl alcohol was also carried out using other bicarbonates and carbonates. The reaction in the presence of cesium bicarbonate and lithium carbonate gave 4-nitrobenzyl acetate in excellent yield, while in the presence of Na2CO3, K2CO3, Cs2CO3, or KHCO3 the yield was in the range of 80%-95%. Calcium carbonate and cobaltous carbonate did not promote the acetylation of 4-ntirobenzyl alcohol using acetic anhydride. The acetylation of 4-nitrobenzyl alcohol was carried out using ethyl acetate, THF, toluene, diethyl ether, dichloromethane and acetonitrile, and gave good yields ranging from 75%-99%. Toluene was the best solvent for the reaction, while diethyl ether was the poorest. © 2013 by the authors; licensee MDPI, Basel, Switzerland.