The Journal of Organic Chemistry

A 1, 6-eliminative epoxide cleavage in the synthesis of an ibuprofen metabolite

RR Kurtz, DJ Houser

Index: Kurtz, Richard R.; Houser, David J. Journal of Organic Chemistry, 1981 , vol. 46, # 1 p. 202 - 203

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Citation Number: 12

Abstract

Previous syntheses of Z-[p-(2-methyl-2-hydroxy-propyl) phenyl] propionic acid (1), lt2 a major human metabolite of ibuprofen (II), were considered unsuitable for preparation of large quantities of pure I which were required for analytical studies. We report here a short, efficient synthesis of 2-[p-(2-methyl-2-hydroxypropyl)-phenyl] propionic acid, I, from ibuprofen, employing a novel 1, 6-eliminative cleavage of an epoxide which may have ...