Acetic Acid → HCID 86638785, compound

Participants

Reaction Steps

A mixture of the crude liquid 1-(4-bromophenyl)-2-hydroxy-2-methyl-propan-1-one (28.0 g, 65% 115 mmol, 74 mmol), malononitrile (35 g, 0.52 mol), acetic acid (0.4 g) and dry pyridine (100 mL) was stirred at room temperature for 24 hrs. The reaction mixture was then poured into 1 L of ice water with vigorous stirring and kept in the refrigerator overnight. The yellow precipitate was collected by vacuum filtration, washed with methanol and dried under vacuum. The product was recrystallized from 70% dichloromethane/methanol. Yield: 10.0 g (40%). mp: 235° C. 1H NMR (400 MHz, CDCl3) δ 1.77 (s, 6H),) 7.58 (d, J=8.4 Hz, 2H), 7.72 (d, J=8.4 Hz, 2H). 13C NMR (100 MHz, (100 MHz, CDCl3) δ 176.55, 174.76, 133.35, 129.40, 129.18 125.89, 111.05, 110.19, 110.05, 99.21, 26.09.

Provenance & Evidence