Autoxidation of 2α-hydroxy-5α-cholestan-3-one in methanolic potassium hydroxide
Abstract
2α-Acetoxy-5α-cholestan-3-one in methanolic potassium hydroxide or in an excess of methanolic potassium carbonate at 20° for 16 hours is converted into a mixture of the monomethyl esters of 2,3-seco-5α-cholestane-2,3-dicarboxylic acid. 5α-Cholestane-2,3-dione is isolated as an intermediate and is probably formed by autoxidation of 2α-hydroxy-5α-cholestan-3-one through 2-hydroperoxy-2-hydroxy-5α-cholestan-3-one.