Sulfuric Acid → 2-Benzoylcyclohexanone

Participants

Reaction Conditions

Reaction Steps

Cumene (dry, 180 mL), sodium tert-pentoxide (35.8 g; 0.326 mol), and methyl benzoate (68.1 g; 0.50 mol) were placed into a four-necked, round bottom, half-liter flask equipped with a stirrer, a thermometer, and a reflux condenser. The mixture was heated to 100° C. and kept at that temperature under a blanket of nitrogen. Cyclohexanone (24.5 g; 0.250 mol) was added slowly over a period of 15 minutes by means of a syringe pump. After 20 minutes from the beginning of the addition of the ketone, the mixture was cooled with an ice water bath to room temperature. Aqueous sulfuric acid (10%) was added with stirring, keeping the temperature below 25° C., until the pH of the aqueous layer was acidic. The organic layer was washed in a one liter separation funnel with aqueous sodium bicarbonate and then with water. The solvents were evaporated on a Rotovap and the residue was crystallized from heptane, affording BCH (38.43 g, 76% yield) having a purity of 99% (GC).

Provenance & Evidence