Hydrochloric Acid → P-Chloroacetophenone

Participants

Reaction Steps

A 50-mL round-bottom flask was equipped with a magnetic stir bar, reflux condenser, thermometer, nitrogen inlet, and heating mantle attached to a temperature controller. The flask was charged with 2,4-diclhloroacetophlenone (5.0 g, 26.5 mmol) and copper(I) chloride (5.24 g, 53.0 mmol). Propionic acid (5.87 g, 79.0 mmol) and N,N-dimethylformamide (20 mL) were added, and the resulting mixture was heated to 130°-135° C. Additional copper(I) chloride was added after 31 hours in order to increase the rate of the reaction. The reaction was monitored by GC analysis and was judged to be complete when the starting material was no longer detectable (100 hours). The reaction mixture was cooled to room temperature; toluene (50 mL) and 2M hydrochloric acid solution (100 mL) were added. The layers were separated, and the upper organic layer was washed with 2M hydrochloric acid solution (50 mL). The resulting yellow organic layer was washed with water (50 mL) and dried over sodium sulfate. The solvent was removed by evaporation under reduced pressure. The residue was dried under vacuum, yielding 3.95 g of 4-chloroacetophenone (3.95 g, 98.9%) as a yellow oil.

Provenance & Evidence