The versatility of Raney nickel as a catalyst in effecting various reductive transformations of organic compounds is quite well known (1, 2). Catalytic oxidations in the presence of Raney nickel, however, are relatively obscure (2,11). Paul (3) and Palfrey (4), for example, have shown that certain secondary alcohols may be dehydrogenated catalytically to the corresponding ketones; however, temperatures up to 250°must be used, and even then yields leave much to be desired. A recent report (5) of work by H. Ruschig at the I. G. Farbenindustrie laboratories has described the catalytic conversion of pregnenolone (I) to pro-COCHs Z\ Axl/V' HO-CO CHS gesterone (II) in the presence of a special Raney nickel catalyst and cyclohexanone as a hydrogen acceptor. The object of the present investigation was to determine the generality of this oxidation and to study the possibility of using it in the reverse sense; i.e., as a reductive method in the presence of a hydrogen donor. The latter phase would constitute an extension of the work of Mozingo et al. ( 12).

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Piperonylic acid reactant: Sixty grams (0.4 mole) of piperonal product: piperonylic acid

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