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

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