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Synthesis 2008(17): 2729-2732  
DOI: 10.1055/s-2008-1067201
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Phenylacetic Acids with 2-Oxoalkyl Substituents in the ortho-Position from o-Phenylenediacetic Acid

Syed Masood Husain, Bernhard Wünsch*
Institut für Pharmazeutische und Medizinische Chemie der Westfälischen Wilhelms-Universität Münster, Hittorfstraße 58-62, 48149 Münster, Germany
Fax: +49(251)8332144; e-Mail: wuensch@uni-muenster.de;
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Publication History

Received 27 March 2008
Publication Date:
24 July 2008 (online)

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Abstract

A one-step procedure for the synthesis of 2-(2-oxoalkyl)-substituted phenylacetic acids is described. Very slow addition of organolithium compounds to o-phenylenediacetic acid is the crucial feature to obtain the desired ε-oxo acids in good yields. The selective formation of the ε-oxo acids from the diacid is explained on the basis of hemiketal anion formation.

Key words

organometallic reagents - polyanions - carboxylic acids - ketones - nucleophilic addition - heterocycles - ε-oxo acids - hemiketal anions