Hydrochloric Acid → P-Chloroacetophenone

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.

1. customA 50-mL round-bottom flask was equipped with a magnetic stir bar
2. temperaturereflux condenser
3. temperaturethermometer, nitrogen inlet, and heating mantle
4. temperaturethe resulting mixture was heated to 130°-135° C
5. temperatureto increase
6. customthe rate of the reaction
7. custom(100 hours)
8. customThe layers were separated
9. washthe upper organic layer was washed with 2M hydrochloric acid solution (50 mL)
10. washThe resulting yellow organic layer was washed with water (50 mL)
11. dry with materialdried over sodium sulfate
12. customThe solvent was removed by evaporation under reduced pressure
13. customThe residue was dried under vacuum

ORD record

ord-45585abbc1a4491aa4f7b028cb55a199

Source dataset

uspto-grants-1999_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05886210