A Convenient Protocol for the Esterification of Carboxylic Acids with Alcohols in the Presence of di-t-Butyl Dicarbonate

Abstract

Stoichiometric mixtures of carboxylic acids and primary or secondary alkyl alcohols are cleanly converted into their corresponding esters by treatment with di-t-butyl dicarbonate [(BOC)₂O] in the presence of catalytic amounts of N,N′-dimethylaminopyridine (DMAP). This convenient procedure provides a general access to a broad variety of esters including those bearing highly sensitive functional groups such as phenol esters or BOC-groups. Purification of the products is particularly easy since the byproducts t-BuOH and CO₂ are volatile - a great advantage over the standard DCC/DMAP method.

Key words

di-t-butyl dicarbonate - esters - esterification - carboxylic acids - catalysis

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