Acetophenone → 3-(4-Fluorophenyl)-1-phenylprop-2-en-1-one

Participants

Reaction Steps

To a mechanically stirred solution of 5.0 g NaOH in 35 ml H2O and 25 ml EtOH at 15° C. was added 12.0 g (0.100 mole) of acetophenone and 12.4 g (0.100 mole) of 4-fluorobenzaldehyde. After a brief exotherm to 25° C., the temperature returned to 15° C., and the cooling bath was removed. The reaction mixture was stirred at room temperature for 1.5 hour, and the thick slurry was transferred to a beaker to cool overnight at 10° C. This mixture was filtered, and the solids were washed with distilled H2O until the washings were neutral to litmus. Upon drying in vacuo, 20.8 g of a pale yellow solid was obtained, m.p. 86°-87° C. IR (Nujol): 1660, 1605, 1590, 1580 cm-1. 1H NMR (200 MHz, CDCl3): δ 7.12 (d, J=16 Hz, 1H), 7.42-7.68 (m, 7H), 7.78 (d, J=16 Hz, 1H), 8.02 (m, 2H).

Provenance & Evidence