Facile Selective Acetylation of Primary Alcohols Using Ethyl Acetate in Acidic Medium

Esters are demanded in a varied range of human industries and, although the classical methods for their production have been known since the late 19(th) century, the search for improved and sustainable protocols to prepare this class of compounds is yet invaluable. An efficient, fast and straightforward method has been stablished, using TsOH and EtOAc for the acetylation of primary alcohols, with yields ranging from 81 to 98 %, depending on the groups near the hydroxyl group. A slight variation of the protocol might also be applied to secondary alcohols with moderate to high yields (65 to 91 %). Finally, the methodology can be used to selectively acetylate primary and secondary alcohols in the presence of tertiary or phenolic hydroxyl groups.