Citric Acid → 4-Hydroxy-2-(4-hydroxybenzyl)-3-methyl-5-propylbenzofuran

Participants

Reaction Steps

Under nitrogen atmosphere, ethanethiol (4.9 g; 80 mmoles) was added dropwise over 5 minutes to a mixture Of 99% sodium hydride (1.9 g; 80 mmoles) in dimethylformamide (100 ml). After stirring for 15 minutes, a solution of 4-hydroxy-2-(4-methoxybenzyl)-3-methyl-5-propylbenzofuran (2.4 g; 8mmoles) in dimethylformamide (5 ml) was added in one portion. The mixture was refluxed for 2 hours, cooled, acidified with 20% citric acid solution and extracted with ether. The ether solution was washed with water, dried (Na2SO4), filtered, concentrated, and chromatographed to obtain 2.2 g of the title compound as an oil which crystallized from an ether hexane mixture.

Provenance & Evidence