INDIRECT ELECTROCHEMICAL SIDE-CHAIN OXIDATION OF ALKYL AROMATIC COMPOUNDS - SELECTIVE SYNTHESIS OF METHYL BENZOATES OR ORTHOBENZOIC ACID TRIMETHYLESTERS

Article abstract of DOI:10.1016/S0040-4020(01)87454-8

The technically important side-chain oxidation of alkyl aromatic compounds to form either methyl benzoates or orthobenzoic acid trimethylesters can be performed electrochemically at low potentials in methanol solution using an undivided cell and tris(2,4-dibromophenyl)amine as redox catalyst.Under neutral or slightly acidic conditions methyl benzoates are selectively formed while under basic conditions the orthoesters are predominating.In a similar way ortho benzoic acid trimethylesters are formed selectively starting from benzaldehyde dimethylacetals.The redox catalyst is stable under the reaction conditions so that several thousand cycles can be performed without noticeable loss.