Hydrochloric Acid → [5-(4-Chlorophenyl)furan-2-yl](cyclopropyl)methanone

Participants

Reaction Steps

To a stirring mixture of 128 g (0.96 mole) of AlCl3 and 720 ml of CS2 was added portionwise 100 g (0.96 mole) of cyclopropanecarboxylic acid chloride while keeping the temperature below 30° by means of an ice bath. A solution of 172 g (0.96 mole) of 2-(4-chlorophenyl)furan in 480 ml of CS2 was added dropwise while maintaining the temperature between 10°-15° with large volume of HCl gas being given off. The reaction mixture was stirred in an ice bath for 15 minutes, allowed to warm to room temperature over a one hour period, and then added to 2000 ml of ice/water. The aqueous layer was separated from the CS2 layer and extracted with 2 × 500 ml portions of CH2Cl2. The CS2 and CH2Cl2 layers were combined, were washed with 1000 ml of 6% Na2CO3 solution and with 1000 ml of water, and then dried over magnesium sulfate. The solvent was removed on a rotary evaporator leaving red-brown residue which was extracted several times with boiling hexane. The combined hexane extracts were cooled and the resulting solid filtered and air dried to yield 41 g (17%) of product. An analytical sample was prepared by recrystallizing a sample from hexane/Darco, m.p. 88°-89°.

Provenance & Evidence