Chloroacetyl chloride → 1-(5-Benzenesulfonyl-2-hydroxy-phenyl)-ethanone

Participants

Reaction Conditions

Reaction Steps

Chloroacetyl chloride (2.35 g; 0.030 mol) was added at 0° C. to a solution of 4-benzenesulfonyl-phenol (2.34 g; 0.010 mol) in carbon disulfide (50 mL). After 10 minutes at ambient temperature, aluminum trichloride was added in small portions. The reaction was heated at 130° C. under reflux, and the carbon disulfide was distilled, after which the reaction was heated at 180° C. for 45 minutes. After cooling to ambient temperature, the mixture was treated with 10% aqueous HCl (25 mL), extracted with ethyl acetate (100 mL×2), dried (Na2SO4) and concentrated in vacuo. The solid residue was purified by column chromatography on silica gel (hexane-ethyl acetate; 7:3) to give 1-(5-benzenesulfonyl-2-hydroxy-phenyl)-ethanone as a white solid (1.924 g; 70%). A sample was recrystallized from ethyl acetate-hexane: MS; (M)+ 276, m. p. 155.5-157.3° C.

Provenance & Evidence