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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 26, 1996 - Issue 3
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Original Articles

The Regioselective 4-Benzylation of 2,4-Dihydroxybenzaldehyde

Wilford L. Mendelson Synthetic Chemistry Department, SmithKline Beecham Pharmaceuticals, Post Office Box 1539, King of Prussia, PA, 19406–0939
,
Monica Holmes Synthetic Chemistry Department, SmithKline Beecham Pharmaceuticals, Post Office Box 1539, King of Prussia, PA, 19406–0939
&
Jack Dougherty Analytical Chemistry Department, SmithKline Beecham Pharmaceuticals, Post Office Box 1539, King of Prussia, PA, 19406–0939
Pages 593-601 | Received 08 Jul 1995, Published online: 21 Aug 2006
 
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Abstract

A regioselective mono-benzylation of the 4-hydroxyl group of 2,4-dihydroxybenzaldehyde (2) to produce 1 under extremely mild basic conditions (NaHCO3 or KF) has been developed. This approach gives improved regioselectivity relative to earlier methods.

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