Bulletin of the Chemical Society of Japan p. 3249 - 3254 (1988)
Update date:2022-08-05
Topics:
Miyano, Sotaro
Fukushima, Hiroshi
Handa, Shigeru
Ito, Hiromitsu
Hashimoto, Harukichi
A partical 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 bolding DMF under dilution conditions.Silica-gel column chromatography allowed ready separation of the intramolecularly coupled cyclic diester (30-60 percent yield) from other by-products accompanying the Ullmann reaction, and alkaline hydrolysis gave unsymmetrical diphenic acid.Axially chiral, unsymmetrical diphenic acids of more than 99 percent enantiomeric excess were obtained from the reaction of mixed diesters prepared from (R)-1,1'-bi-2-naphthol.
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