Water → 6-Fluoro-1,2,3,4-tetrahydronaphthalen-2-one

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Reaction Conditions

Reaction Steps

p-Fluorophenylacetyl chloride (17.25 g) in dichloromethane (100 ml) was added dropwise to aluminium chloride (26.7 g) suspended in dichloromethane (400 ml) maintained at -10° C. by cooling in a solid carbon dioxide/acetone bath. Ethylene gas was then passed through the mixture for 15 minutes while maintaining the temperature at -10° C. The mixture was then allowed to warm to room temperature and stirred for 3 hours. The mixture was then cooled to 5°-10° C. and ice and water (160 ml) added cautiously with stirring over a period of 45 minutes. The dichloromethane was then separated and washed successively with dilute hydrochloric acid, (150 ml×2), sodium bicarbonate solution (150 ml×2) and brine. The dichloromethane was then dried and evaporated. The residue was distilled to give 6-fluoro-2-tetralone (12.81 g) with a boiling range of 68°-76° C./0.05 Torr. The distillatte crystallised on standing.

Provenance & Evidence