Acetic Acid → 3-Acetyl-3-phenylfuran

Participants

Reaction Steps

3-Phenylfuran (4.3 g) was dissolved in 80 ml of acetonitrile under argon and treated while stirring with 8.6 g of the mixed anhydride from acetic acid and p-toluenesulphonic acid. The reaction solution was stirred at room temperature for 64 hours and subsequently stirred with 150 ml of saturated sodium hydrogen carbonate solution and 150 ml of diethyl ether 30 minutes. The phases were separated and the aqueous phase was extracted once with a further 100 ml of diethyl ether. The organic phases were combined, washed with 100 ml of water, dried over MgSO4 and freed from solvent. The residue was chromatographed on 200 g of silica gel with methylene chloride/hexane (1:1) as the eluent. There was obtained 0.7 g (13%) of 2-acetyl-4-phenylfuran besides 2.4 g (43%) of 3-acetyl-3-phenylfuran. The former was processed without further purification.

Provenance & Evidence