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The preparative electroreduction of the three methyl monochlorobenzoates, the six methyl dichlorobenzoates, and methyl 2,3,4-trichlorobenzoate in different solvent-supporting electrolytes (SSE) was studied. The rate of the dechlorination, which is the main reaction, is dependent on the substitution pattern. Pronounced regioselectivity is therefore observed in case of the oligochloro derivatives. Hydrogenation of the benzene ring and reduction of the methoxycarbonyl group with formation of a hydroxymethyl group are observed as side-reactions. Quantum chemical calculations on the reaction mechanism were performed. The theoretical results are in accordance with the experimental observations.

Electroreduction of Organic Compounds, 36 [1]. Electroreduction of Chlorinated Methyl Benzoates