THE SYNTHESIS OF SOME DERIVATIVES OF 3,4-METHYLENEDIOXYBENZENE

Abstract

A few derivatives of 3,4-methylenedioxy-α-nitromethylbenzyl alcohol (I) have been prepared. Chlorination with hydrochloric acid and potassium chlorate gave 6-chloro-3,4-methylenedioxy-α-nitromethylbenzyl alcohol (II) which on refluxing with acetic anhydride and sodium acetate gave 6-chloro-3,4-methylenedioxy-ω-nitrostyrene (III). Attempted reduction of (I) with ammonium formate resulted in dehydration to give 3,4-methylenedioxy-ω-nitrostyrene (IV). Reduction of (I) with hydrazine hydrate gave an isobenzaldoxime (VI).β-(3,4-Methylenedioxyphenyl) serine (VII) was prepared by the condensation of piperonal with glycine. α,β-Dibromo-β-(3,4-methylenedioxyphenyl) propionic acid could not be aminated by a dilute aqueous solution of ethylamine. Decarboxylation and elimination of HBr took place to give ω-bromo-3,4-methylenedioxystyrene (VIII).