Hydrochloric Acid → HCID 53879354, compound

Participants

Reaction Steps

Into a round bottom three-necked flask equipped with a stirrer, a reflux condenser, and a dropping funnel were placed 583 g. of anisole, 720 g. of aluminum chloride, and 2.37 liters of carbon disulfide. The reaction solution was stirred and 565 g. of crotonyl chloride were added by dropwise addition at such a rate as to maintain a continuous reflux. As the reaction mixture thickened, an additional 2.37 liters of carbon disulfide were added. The resulting reaction mixture which had the consistency of a slurry was refluxed for 4 hours and thereafter was poured into a mixture of 9 kg. of ice, 2 liters of water and 900 ml. of concentrated hydrochloric acid. The carbon disulfide was removed from the dilute acidified reaction mixture under vacuum. The aqueous residue was then extensively extracted with dichloromethane. The extract was washed with water and dried and was then evaporated in vacuo to yield the condensation product, p-methoxyphenyl propenyl ketone as an oil having a boiling point of about 135° C. (0.5 mm).

Provenance & Evidence