Thionyl Chloride → HCID 19899194, compound

Participants

Reaction Steps

82 g of 3,3-dimethyl-5-phenylvaleric acid are treated with 57 ml of thionyl chloride and heated to reflux for half an hour. Thereafter, the excess reagent is evaporated, finally under a high vacuum for 1.5 hours. The acid chloride prepared, dissolved in 300 ml of methylene chloride, is added within 3.5 hours under an argon atmosphere to 79 g of aluminum trichloride in 650 ml of methylene chloride. Thereafter, the reaction mixture is stirred for an additional 10 minutes and poured on to ice. The organic phase is washed with water dried and evaporated. After chromatography on silica gel with petroleum ether (low-boiling)/ethyl acetate (98:2), there are obtained 62 g of 6,7,8,9-tetrahydro-7,7-dimethyl-5H-benzocycloheptene-5-one.

Provenance & Evidence