Hydrochloric Acid → 1-Phenyl-1,5-hexanedione

Participants

Reaction Conditions

Reaction Steps

To a -10° C. solution of 4-acetylbutyric acid (1 mm, 130 mg) in benzene (1.5 cc) and dichloromethane (1.5 cc) was added oxalyl chloride (1.1 mm, 140 mg) followed by a drop of N,N-dimethylformamide; the mixture was then brought to 25° C. for 30 minutes. It was then cooled to -10° C. and AlCl3 (2 mm, 266 mg) was added portion wise and the mixture held at 0° C. for 1 hour. Ice was added, followed by 1N HCl. Then the product was extracted with ethyl acetate (2×10 cc). The organic phase was washed with dilute NaHCO3 /brine and the solvents removed in vacuo to afford the title compound.

Provenance & Evidence