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Synlett 2004(13): 2391-2393
DOI: 10.1055/s-2004-832828
DOI: 10.1055/s-2004-832828
LETTER
© Georg Thieme Verlag Stuttgart · New York
A Convenient Procedure for Parallel Ester Hydrolysis
Further Information
Received
15 July 2004
Publication Date:
28 September 2004 (online)
Publication History
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.
Key words
ester hydrolysis - deprotection - parallel synthesis - barium hydroxide octahydrate - 9-chloroacridine
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References
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%).