Preparation of N‐Alkylacetamides by the Anodic Oxidation of Carboxylic Acid Salts

Abstract

The possibility of preparing N‐alkylacetamides by the electrolytic oxidation of carboxylate ions at a carbon anode in the presence of acetonitrile has been investigated. A yield of substituted acetamide of about 50% was obtained with potassium valerate, but it gradually dropped to zero in favor of the Kolbe coupled product in going from potassium octanoate to potassium laurate. An explanation of this effect involving specific orientation of the adsorbed long chain carboxylates on the electrode surface is included. Products derived from intermediate carbonium ions were found, and a mechanism for their formation is proposed.