Asymmetric synthesis of axially chiral, unsymmetrical diphenic acids via intramolecular Ullmann coupling reaction

…, H Fukushima, S Handa, H Ito, H Hashimoto

Index: Miyano, Sotaro; Fukushima, Hiroshi; Handa, Shigeru; Ito, Hiromitsu; Hashimoto, Harukichi Bulletin of the Chemical Society of Japan, 1988 ,  vol. 61, p. 3249 - 3254

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Citation Number: 61

Abstract

A practical route to unsymmetrical diphenic acids is described. Successive esterification of ethylene glycol with two different 2-halobenzoyl chlorides gave the corresponding mixed diester, which was treated with copper powder in boiling DMF under dilution conditions. Silica-gel column chromatography allowed ready separation of the intramolecularly coupled cyclic diester (30–60% yield) from other by-products accompanying the Ullmann reaction, ...