Electrolytic Reduction in Liquid Ammonia

Abstract

BENZENOID compounds have been reduced to dihydro-derivatives by means of sodium and alcohol in liquid ammonia¹. The process has now been carried out electrolytically on m-tolyl methyl ether at a smooth copper cathode with a current density of 0.04 amp./sq. cm. in a saturated solution of sodium ethoxide in liquid ammonia containing 5 percent of ethyl alcohol, the temperature being maintained at about 40° by means of a solid carbon dioxide–alcohol bath. The dihydro-m-tolyl methyl ether, probably the 2 : 5-, was identified (see ref. 1) by conversion to the 2 : 4-dinitrophenyl-hydrazone of 3-methyl-Î"²-cyclohexenone, m.p. 174°, undepressed by an authentic specimen. The current efficiency of the reduction was low, but can probably be improved, and the process may be of general utility for similar reactions.