Mild and Chemoselective Deacetylation Method Using a Catalytic Amount of Acetyl Chloride in Methanol

Efficient deacetylation of alcohol acetates under mild acidic conditions was accomplished with a catalytic amount of acetyl chloride in methanol. Acetates of various primary, secondary, aromatic and sugar alcohols were successfully deprotected. Highly chemoselective removal of acetyl groups in presence of other commonly employed esters was also achieved in excellent yields. The reactivity of this transesterification-mediated deacetyl ation was found to be directly dependent upon the electronic and steric nature of the acetates.