Acetone → 1,5-Bis(2-hydroxyphenyl)-1,4-pentadien-3-one

Participants

Reaction Steps

2-Hydroxybenzaldehyde (1q, 1.81 ml, 17.0 mmol) and acetone (19, 0.62 ml, 8.4 mmol) were combined in ethanol (15 ml) and stirred for 15 min at room temperature. A solution of sodium hydroxide (1.00 g, 25.0 mmol) and water (4 ml) was added and the solution stirred for 1 week at room temperature. The mixture was neutralized with hydrochloric acid (1 N) and the resulting precipitate filtered and recrystallized from ethyl acetate/hexane to give 1.79 g (80%) of a yellow solid: mp 154-157° C. [expected mp 155° C.]; 1H NMR: (DMSO) δ 6.89 (m, 4H), 7.27 (m, 4H), 7.68 (d, 2H, J=7.4 Hz), 7.93 (d, 2H, J=16.1 Hz), 10.22 (s, 2H); 13C NMR: (DMSO) δ 116.1, 119.3, 121.3, 125.3, 128.5, 131.5, 137.6, 156.9, 188.5.

Provenance & Evidence