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

Participants

Reaction Conditions

Reaction Steps

A solution of sodium nitrite (1.63 g) in water (4.3 ml) was added dropwise to a solution of 4'-amino-3'-chloroacetophenone (2.5 g) and concentrated hydrochloric acid (5.5 ml) in water (5.5 ml) at 0° to 3° C., and the solution was stirred for 15 minutes at 0° C. The resulting solution was added portionwise to a mixture of sodium nitrite (7.3 g) and cuprous oxide (0.76 g) in water (32 ml) at -5° to 0° C. The mixture was stirred for 1 hour at 0° C. and for 1 hour at room temperature, and extracted with chloroform. The extract was washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to column chromatography on silica gel (60 g) eluting with chloroform. The fractions containing the desired compound were combined and concentrated under reduced pressure to give pale yellow crystals of 3'-chloro-4'-nitroacetophenone (2.2 g).

Provenance & Evidence