Benzaldehyde → 1-(4-Carboxyphenyl)-3-phenyl-2-propen-1-one

Participants

Reaction Steps

4-Acetylbenzonitrile (44al, 1.00 g, 6.9 mmol) and sulfuric acid (4 ml) were combined in water (4 ml) and the mixture stirred for 2.5 hr at reflux. The resulting mixture was extracted into ethyl acetate, washed with saturated sodium chloride, dried over magnesium sulfate, filtered and evaporated to give 0.98 g (87%) of compound 44ad as a white solid: mp 204° C.; 1H NMR: (DMSO) δ 2.61 (s, 3H), 8.04 (s, 4H), 13.23 (s, 1H). The solid (44ad, 0.50 g, 3.0 mmol) and sodium hydroxide (0.29 g, 7.3 mmol) were combined in water (4 ml) and ethanol (4 ml) and stirred for 30 min at room temperature. Benzaldehyde (1b, 0.31 ml, 3.1 mmol) was added and the mixture stirred for 48 hr at room temperature. The resulting mixture was acidified with hydrochloric acid (1 N), extracted into ethyl acetate, washed with saturated sodium chloride, dried over magnesium sulfate, filtered and evaporated to a afford a solid. The crude solid was recrystallized from ethyl acetate to give 0.54 g (70%) of a yellow solid: mp 217-220° C. [expected mp 217-220° C.]; 1H NMR: (DMSO) δ 7.45 (m, 5H), 7.76 (d, 1H, J=16.1 Hz), 7.93 (d, 1H, J=15.5 Hz), 8.09 (d, 2H, J=7.9 Hz), 8.23 (d, 2H, J=7.6 Hz) 13.34 (s, 1H); 13C NMR: (DMSO) δ 121.9, 128.5, 128.8, 128.9, 129.4, 130.6, 134.3, 134.4, 140.6, 144.6, 166.4, 188.8.

Provenance & Evidence