Toluene → 4-Chloro-4'-methylbutyrophenone

Participants

Reaction Steps

To a solution of 100 g (1.1 mole) of toluene and 146 ml (1.3 mole) of 4-chlorobutyryl chloride in 470 ml of carbon disulfide at 10° C. under N2, is added in portions, 180 g (1.4 mole) of aluminum chloride. Stir 1 hr. at 0° C., then discontinue the stirring and allow the reaction mixture to settle for 1/2 hr. Decant the top carbon disulfide layer and pour the lower layer into concentrated HCl/ice. Extract with two 600 ml portions of methylene chloride. The combined extracts are washed with 1 L of 10% potassium bicarbonate, dried over sodium sulfate and concentrated in vacuo to provide the title compound.

Provenance & Evidence