Dimethyl Sulfoxide → 3-(2-Propenyl)-2-tetralone

Participants

Reaction Conditions

Reaction Steps

A mixture of 3,4-dihydro-2-hydroxy-3-(2-propenyl)-naphthalene carboxylic acid, methyl ester (46.1 g, crude), dimethyl sulphoxide (132 ml), water (5 ml) and lithium chloride (9.5 g, 226 mmol) was heated at 125° C., with stirring, under argon for 4.5 h. The mixture was cooled and diluted with water (750 ml) and extracted with ethyl acetate (3×1000 ml). The combined extracts were washed with water (1000 ml) and brine (1000 ml), dried (Na2SO4) and evaporated in vacuo to give a brown oil (35.5 g). This was chromatographed on silica eluting with 10% ether-hexane to give the title compound as a brown oil (25.9 g, 74%).

Provenance & Evidence