Sulfuric Acid → 2-(2'-Chlorophenyl)-1,3-cyclohexanedione

Participants

Reaction Conditions

Reaction Steps

A 500 ml round bottom flask was charged with 10.0 g (0.0416 mol) of 6-(2'-chlorophenyl)-5-ketohexanoic acid and 100 ml of 72% sulfuric acid. The reaction mixture was stirred and heated to 120° C. for 51/2 hours (oil bath), then poured into 600 ml of an ice water mixture. A tacky, white solid formed, and this was extracted into 300 ml of methylene chloride. The CH2Cl2 was washed six times with water, dried over anhydrous MgSO4 and stripped to leave 8.87 g of a tacky, white solid. This material was recrystallized from ethyl acetate to give 5.85 g (63%) of 2-(2'-chlorophenyl)-1, 3-cyclohexanedione as a white, crystalline solid, m.p. 148.5°-149° C.

Provenance & Evidence