Non-Kolbe Electrolysis Using Solid-Supported Bases

Significance

A novel electrolytic system for anodic methoxylation of carboxylic acids using silica gel supported bases (e.g. piperidine) was developed. Non-Kolbe electrolysis of carboxylic acid 1 proceeded smoothly to provide methoxylated product 2, which was easily isolated by simple evaporation of the filtrate after the removal of the silica gel supported piperidine. The reuse of silica gel supported piperidine was successfully carried out five times under the same conditions. The various carboxylic acids were examined to give the corresponding methoxylated products in excellent yields (5 examples, 94-100% yields).