Anisole → 4-Propanoylanisole

Participants

Reaction Steps

While 49.3 g (370 mmol) of aluminium chloride were added to 200 ml of dichloromethane and stirred, 40 g (370 mmol) of anisole were slowly added in droplets at 5° C. Subsequently, 32 ml (370 mmol) of propionyl chloride were slowly added in droplets for 30 min, and stirring was further continued at room temperature for 2 hr. After the reaction was completed, the resultant reaction mixture was diluted with dichloromethane, and then washed with a saturated aqueous solution of sodium bicarbonate and water at 5° C. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. Organic residue was purified with column-chromatography in which the mixture of ethyl acetate and n-hexane (1:10) were used as a eluent, thus obtaining 59.5 g (yield: 98%) of a title compound (7).

Provenance & Evidence