Abstract
meso-Tetra(2,6-dichloro-3-sulfonatophenyl)porphyrin iron chloride catalyzes the oxidation of 3,4-dimethoxybenzyl alcohol (veratryl alcohol) in aqueous solution to give veratraldehyde along with demethoxylation and ring-cleavage products. The isolation of a direct ring-cleavage product from the oxidation of veratryl acetate in aqueous solution supports the previously proposed ring-cleavage mechanisms. The oxidation in methanol, however, does not lead to ring-cleavage products. When veratryl alcohol was oxidized in methanol, solvent was found to be incorporated into the 3-position of veratryl alcohol, giving new insight into the mechanism of oxidation.
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