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

Beteiligte Stoffe

Reaktionsschritte

A 5-carboxymethyl-4-(3,4-disubstituted phenyl)-2-mercaptothiazole derivative can be produced by reacting veratrole with succinic anhydride in the presence of anhydrous aluminum chloride to obtain 3-(3,4-dimethoxybenzoyl)propionic acid, subjecting the propionic acid to demethylation with hydrobromic acid to obtain 3-(3,4-dihydroxybenzoyl)propionic acid, then, subjecting it 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 reacting the propionate with ammonium dithiocarbamate to obtain the desired product.

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