Hydrochloric Acid → HCID 21425053, compound

Participants

Reaction Steps

To a stirring mixture of 62 g (0.50 mole) of AlCl3 in 375 ml of 1,2-dichloroethane was added portionwise 75 g (0.5 mole) of 3-carbomethoxypropionyl chloride while keeping the temperature below 25° by means of an ice bath. The reaction mixture was cooled to 15° and a solution of 89 g (0.5 mole) of 5-(4-chlorophenyl)furan in 250 ml of 1,2-dichloroethane was added dropwise with HCl gas being evolved and the temperature rising to 30°. The reaction mixture was stirred at ambient temperature for 1 hour and then added to 1000 ml of ice/water. The organic layer was separated and the aqueous layer extracted with dichloromethane. The combined organic layers were washed with 1000 ml of 6% sodium carbonate solution with 1000 ml of water and dried over MgSO4. The solvent was removed on a Calab evaporator yielding a residual oil which was extracted several times with refluxing hexane. The hexane extracts were cooled to yield a solid which was filtered, washed twice with 6% sodium carbonate solution, recrystallized from hexane and air dried to yield 7 g (5%). An analytical sample was prepared by drying a sample in a vacuum pistol at room temperature, m.p. 99°-100°.

Provenance & Evidence