Hydrochloric Acid → 3-(5-Chloro-2-methoxybenzamido)-2,2-dimethyl-7-methoxy-4-chromanol

Participants

Reaction Conditions

Reaction Steps

A suspension of 25 g (64 mmol) of 3-(5-chloro-2-methoxybenzamido)-2,2-dimethyl-7-methoxy-4-chromanone and 1.24 g (32 mmol) of powdered sodium borohydride in 100 ml of ethanol was stirred at 50° C. for 3 hours, during which the solid dissolved. After cooling, the solution was then poured into ice-water acidified with hydrochloric acid, and extracted with methylene chloride. The organic solution was washed with water, dried and evaporated. The resulting 3-(5-chloro-2-methoxybenzamido)-2,2-dimethyl-7-methoxy-4-chromanol (diastereomer mixture) melted from 165° C.

Provenance & Evidence