Acetyl chloride → Ethyl 5-(4-acetylphenyl)benzofuran-2-carboxylate

Participants

Reaction Steps

12.2 g of acetyl chloride was added to a mixture of 10.3 g of 1B, and 120 ml of carbon disulfide, then 21.8 g of anhydrous aluminum chloride was added in portions to the stirred mixture. The mixture then was stirred at room temperature for 2.5 hours, the temperature rising to 32° C. The mixture was poured into 1 liter of ice water, and stirred for 30 minutes, and the solution was extracted with ether. The extract was dried (MgSO4) and concentrated. The residue was washed with ether and dissolved in 100 ml of chloroform. The solution was treated with activated charcoal, and 100 ml of hexane was added. The resulting solution was concentrated to about 100 ml and cooled to give ethyl 5-(4-acetylphenyl)-benzofuran-2-carboxylate (10A), mp: 105°-107° l C.

Provenance & Evidence