Thionyl Chloride → 3,3-Bis(2-methoxyphenyl)-2-propenenitrile

Participants

Reaction Conditions

Reaction Steps

Thionyl chloride (4.5 mL) was added to a stirred suspension of beta-hydroxy-beta-(2-methoxyphenyl)-2-methoxybenzenepropanenitrile (13.45 g) in dry pyridine (70 mL) maintained at 10° C. during the addition. The reaction was stirred at room temperature for 2 hours, then was diluted with ice-water and extracted with dichloromethane. The organic extract was washed with 3N HCl (1×150 mL; 1×20 mL) and brine and then was dried (MgSO4) and evaporated. The residue was crystallized from isopropanol-hexane to provide 9.0 g of 3,3-bis(2-methoxyphenyl)-2-propenenitrile, mp 99°-100° C. Recrystallization of a portion from the same solvents afforded the analytical sample, mp 100.5°-101.5° C.

Provenance & Evidence