A Convenient Procedure for Parallel Ester Hydrolysis

Marc O. Anderson; Jamie Moser; John Sherrill; R. Kiplin Guy

doi:10.1055/s-2004-832828

LETTER

A Convenient Procedure for Parallel Ester Hydrolysis

Marc O. Anderson^a, Jamie Moser^a, John Sherrill^a, 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;

Abstract

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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.

Key words

ester hydrolysis - deprotection - parallel synthesis - barium hydroxide octahydrate - 9-chloroacridine

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Referenzen

References

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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%).