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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 23, 1993 - Issue 1
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Original Articles

Syntheses and Synthetic Studies of 2-Hydroxy-5-(propargyloxy)benzoic Acid

Alan B. Brown Samuel M. McElvain Laboratories of Organic Chemistry, Department of Chemistry, University of Wisconsin-Madison, Madison, Wisconsin, 53706
&
Howard W. Whitlock Jr. Samuel M. McElvain Laboratories of Organic Chemistry, Department of Chemistry, University of Wisconsin-Madison, Madison, Wisconsin, 53706
Pages 23-34 | Received 13 Jul 1992, Published online: 24 Sep 2006
 
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Abstract

The title compound 1 is best made by selective 5-O-propargylation of methyl gentisate, followed by in situ saponification. Direct propargylation of gentisic acid gives a mixture of propargyl ethers, which surprisingly includes the 2-monoether.

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