Oxidation of 3-hydroxy-1-methyloestra-1,3,5-(10)-triene-11,17-dione (1) with dichlorodicyanobenzoquinone (DDQ) in aqueous dioxan gives the 9β-hydroxy-derivative (2) by a mechanism involving addition of water to the intermediate quinone methide (4).
G. M. Buchan, J. W. A. Findlay and A. B. Turner, J. Chem. Soc., Chem. Commun., 1975, 126 DOI: 10.1039/C39750000126
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