Citric Acid → 2-(p-Methoxybenzyl)-3-methyl-4-hydroxy-5-propylbenzofuran

Participants

Reaction Steps

A mixture of 4-hydroxy-2-(4-methoxybenzoyl)-3-methyl-5-propylbenzofuran (7.2 g; 22 mmoles), potassium hydroxide pellets (8.7 g; 155 mmoles), ethylene glycol (100 ml) and 99% hydrazine (3.0 ml) was heated with stirring and maintaining the internal temperature between 130° C. and 150° C. for 4 hours. The internal temperature was permitted to rise to 175° C. for 1 hour and excess water was always allowed to escape. The mixture was cooled and poured into excess 20% citric acid solution. The mixture was extracted with ether, washed with water, dried (Na2SO4), filtered, concentrated, and chromatographed to give 4 grams of the title compound.

Provenance & Evidence