Practical one-pot conversion of 17b -estradiol to 10 b -hydroxy- (p-quinol) and 10 b -chloro-17 b -hydroxyestra-1,4-dien-3-one

An efficient one-pot procedure for the preparation of 10 beta,17 beta-dihydroxyestra-1,4-dien-3-one (p-quinol, 1, 75%) is reported, involving oxidation of 17 beta-estradiol with potassium permanganate. Similar treatment of 17 beta-estradiol with sodium chlorite led to 10 beta-chloro-17 beta-hydroxyestra-1,4-dien-3-one (2) in 44% yield along with smaller amounts 4-chloro-10 beta,17 beta-dihydroxyestra-1,4-dien-3-one (3), 2, 10 beta-dichloro-17 beta-hydroxyestra-1,4-dien-3-one (4), and 4,10 beta-dichloro-17 beta-hydroxyestra-1,4-dien-3-one (5). (c) 2006 Elsevier Inc. All rights reserved.