Acetophenone → HCID 18690517, compound

Participants

Reaction Conditions

Reaction Steps

A 500 mL, 4 neck round bottom flask equipped with mechanical stirring, a nitrogen inlet, a thermometer, a condenser and an addition funnel was charged with 60% sodium hydride in mineral oil (20.5 g. 0.51 mol), methyl neo-octanoate (92.3 g., 0.58 mol, prepared from neo-octanoic acid, a product of Exxon), and xylene (42.8 g.). The mixture was heated to reflux (135° C.), and then a solution of acetophenone (32.4 g. 0.27 mol) in xylene (19.1 g.) was added over 1.25 h. The mixture was kept at reflux for an additional 1 h. After cooling to room temperature, the reaction was quenched by the careful addition of methanol (20 mL), and then acidified with 150 g/L sulfuric acid (180 mL). After separation of layers, the organic phase was washed with water (2×100 mL) and brine (100 mL). After drying by passing through anhydrous sodium sulfate, the solution was concentrated in vacuo at 70° C. down to 12 mbar to yield an orange liquid containing product in a crude yield of 63%. Vacuum distillation (200 mtorr) through a 15 cm Vigreux column yielded the product in the heart cut: 1-phenyl-3-neoheptyl-1,3-propanedione (X) (37.2 g., 96% pure, 0.14 mol; 53% yield; bp: 94-135° C.). Dypnone, the self-condensation product of acetophenone was undetectable in the product.

Provenance & Evidence