Veratrole → 4-(3,4-Dimethoxyphenyl)-4-oxobutanoic acid

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Reaction Steps

A 5-carboxymethyl-2-mercaptothiazole derivative can be prepared by reacting veratrole with succinic anhydride in the presence of anhydrous aluminum chloride to obtain 3-(3,4-dimethoxybenzoyl)propionic acid, subjecting the compound to demethylation with hydrobromic acid to obtain 3-(3,4-dihydroxybenzoyl)propionic acid, subjecting the compound to enol-lactonation in the presence of acetic anhydride and sodium acetate, reacting the resulting compound sequentially with N-bromosuccinimide and with diphenyldiazomethane to obtain 3-(3,4-diacetoxybenzoyl)-3-bromopropionate, and further reacting the compound with ammonium dithiocarbamate.

Provenance & Evidence