Thionyl Chloride → 3beta-Acetoxychol-5-enyl chloride

Participants

Reaction Steps

3β-Acetoxychol-5-enic acid (500 g; 1.2 moles) was added to 8 liters of anhydrous benzene obtained by dehydration with a molecular sieve. The resulting solution was cooled with ice, and with stirring, 390 ml (5.4 moles) of thionyl chloride was added dropwise. After the addition, the mixture was stirred at room temperature for 4 hours. The reaction mixture was concentrated under reduced pressure, and 2 liters of anhydrous benzene resulting from dehydration with a molecular sieve was added to the residue. The mixture was repeatedly concentrated under reduced pressure (five times) to remove the thionyl chloride contained in the residue. The resulting solid crude product, 3β-acetoxychol-5-enyl chloride, was used in the subsequent step as a starting compound without purification.

Provenance & Evidence