Synlett 2004(13): 2391-2393  
DOI: 10.1055/s-2004-832828
LETTER
© Georg Thieme Verlag Stuttgart · New York

A Convenient Procedure for Parallel Ester Hydrolysis

Marc O. Andersona, Jamie Mosera, John Sherrilla, R. Kiplin Guy*a,b
a Department of Pharmaceutical Chemistry, University of California at San Francisco, San Francisco, CA 94143-2280, USA
b Department of Cellular and Molecular Pharmacology, University of California at San Francisco, San Francisco, CA 94142-2280, USA
Fax: +1(415)5140689; e-Mail: rguy@cgl.ucsf.edu;
Further Information

Publication History

Received 15 July 2004
Publication Date:
28 September 2004 (online)

Abstract

The treatment of alkyl esters with barium hydroxide ­octahydrate in methanol followed by protonation with anhydrous hydrogen chloride affords carboxylic acids. The procedure does not require aqueous workup and is particularly suitable for parallel ­synthesis applications.

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Typical Procedure: A solution of ethyl salicylate (0.161 g, 0.968 mmol) in MeOH (10 mL) was treated with BaOH·8H2O (0.458 g, 1.45 mmol, 1.5 equiv) and heated to 80 °C for 2 h. Solvent was removed in vacuo, followed by the addition of HCl (1 M in Et2O) (10 mL) and MgSO4, and the mixture was filtered, and concentrated to afford salicylic acid (0.115 g, 87%).