Hydrochloric Acid → 1-(3,5-Dichloro-4-methylphenyl)ethan-1-one

Participants

Reaction Steps

18.8 g (0.24 mole) of acetyl chloride were added dropwise, with ice-cooling and stirring, to a suspension of 34.7 g (0.26 mole) of anhydrous aluminium chloride powder in 150 ml of 1,2-dichloroethane. The mixture was stirred, with ice-cooling, for a further 30 minutes, after which 18.4 g (0.2 mole) of toluene were added dropwise, with stirring, over a period of about 20 minutes, whilst maintaining an internal temperature below 5° C. Stirring was continued for a further 1 hour, after which 23 ml of liquified chlorine, trapped in dry ice/acetone, were blown little by little over a period of 4 hours into this mixture, whilst maintaining it at an internal temperature of from 5° to 10° C. by ice-cooling. When the addition was complete, the mixture was stirred at 5°-10° C. for a further 30 minutes, after which the reaction mixture was poured into a mixture of 50 ml of concentrated hydrochloric acid and 500 g of broken ice. The mixture was then extracted with 500 ml of diethyl ether and the extract was washed with water and then dried over anhydrous sodium sulphate. The solvent was then distilled off, giving 47.9 g of a crude product, which was then subjected to column chromatography through silica gel, eluted with a 1:1 by volume mixture of hexane and benzene, to give 22.8 g (yield 56.1%) of the desired 3,5-dichloro-4-methylacetophenone, melting at 64°-66° C. and boiling at 108°-111° C./400 Pa (3 mmHg).

Provenance & Evidence