Electrochemical hydrogenation of citral 1. The role of the copper cathode in the electroreduction of citral

Article abstract of DOI:10.1007/BF00698997

Alcohols (citronellol and isomeric nerol and geraniol) are the main products of the electroreduction of citral at the copper cathode in the presence in the AcOH in a water-DMF medium.It has been suggested that under the conditions of the electrolysis at the hydrogen reduction potential (E = -1.2 V) electroreduction of citral occurs according to the electrochemical hydrogenation mechanism.The total yield of the alcohols and the selectivity of the process depend on the preliminary treatment of the cathode.The electroreduction of citral at a mechanically cleaned cathode gives alcohols in 54percent total yield, and unsaturated alcohols are the prevailing products.Preliminary annealing of the cathode results in an increase in the total yield of alcohols in the electrolysis to 86percent and in the predominant formation of citronellol. - Key words: copper cathode, citral, citronellol, electrochemical hydrogenation, electroreduction, recrystallization.