Hydrochloric Acid → 1-(3-Chloro-4-cyclohexylphenyl)ethanone

Participants

Reaction Steps

Solution of sodium nitrite (1.2 g, 0.017 mol) in demineralized water (7 mL) is added to a solution of 1-(3-amino-4-cyclohexylphenyl)ethanone (3.4 g, 0.016 mol) in concentrated hydrochloric acid (34 mL) at 0-5° C. & is allowed to stir for 15 minutes at this temperature. It is then poured into a slurry of cuprous chloride (3.1 g, 0.03 mol) in demineralized water (10 mL) at 60-65° C. & stirred for 30 minutes. The reaction mixture is extracted in ethyl acetate (2×30 mL). Combined organic layer is dried over sodium sulfate and concentrated to get the crude, which is purified using column chromatography (230-400 mesh; toluene:n-hexane, 3:2) to yield 1-(3-chloro-4-cyclohexyl-phenyl)ethanone.

Provenance & Evidence