Hydrochloric Acid → HCID 12585191, compound

Participants

Reaction Steps

A mixture of anisole (8.67 g., 0.08 mole), 4-nitrobenzoyl chloride (16.4 g., 0.088 mole) and methylene chloride (80 ml). at 5° was stirred vigorously and treated with finely powdered aluminum chloride (11.2 g., 0.084 mole). The reaction mixture was stirred at room temperature for 20 hrs. and then decomposed with ice and hydrochloric acid (15 ml.). The aqueous solution was extracted twice with methylene chloride. The combined methylene chloride solution was washed with aqueous sodium bicarbonate solution and finally with water. The organic layer was dried (MgSO4) and filtered. The solvent was removed in vacuo, and the residue on triturating with methanol gave the product, m.p. 121°-122°. This product was used in the next step without purification. 4-(4-nitrobenzoyl)-2-chloroanisole and 4-(4-nitrobenzoyl)-3-chloroanisole were prepared by the same procedure.

Provenance & Evidence