Synlett 2004(2): 0263-0266  
DOI: 10.1055/s-2003-44986
LETTER
© Georg Thieme Verlag Stuttgart · New York

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

Lukas J. Gooßen*, Arno Döhring
Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mülheim an der Ruhr, Germany
Fax: +49(208)3062985; e-Mail: goossen@mpi-muelheim.mpg.de;
Further Information

Publication History

Received 12 November 2003
Publication Date:
08 December 2003 (online)

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.