Preparation of the 5-methyladamantan-2-ols and the 2,5-dimethyladamantan-2-ols

Abstract

The oxidation of 1-methyladamantane, 3-methyladamantan-1-ol, or 2-methyladamantan-2-ol, with sulphuric acid is a more complex process than has previously been realised, but it gives 5-methyladamantanone as the major product. Reduction of the ketone affords the corresponding secondary alcohols, and a variety of methods provide the related methyl-carbinols. None of these reactions is usefully stereospecific, and the separation of the mixtures obtained, although successfully accomplished, is exceptionally difficult.