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

Participants

Reaction Steps

4-Hydroxybenzaldehyde (1f, 2.00 g, 16.4 mmol) and acetone (19, 0.61 ml, 8.3 mmol) were combined in ethanol (30 ml) and stirred for 15 min at room temperature. A solution of sodium hydroxide (1.00 g, 25.0 mmol) and water (30 ml) was added and the mixture stirred for 4 hr at room temperature. The resulting mixture was extracted into ethyl acetate, washed with saturated sodium chloride, dried over magnesium sulfate, filtered and evaporated to afford a solid. The crude solid was recrystallized from ethyl acetate/hexane to give 0.85 g (39%) of a yellow solid: mp 235-237° C. [expected mp 238-239° C.]; 1H NMR: (DMSO) δ 6.82 (d, 4H, J=8.5 Hz), 7.08 (d, 2H, J=16.1 Hz), 7.61 (d, 4H, J=8.5 Hz), 7.64 (d, 2H, J=15.7 Hz), 10.08 (s, 2H); 13C NMR: (DMSO) δ 115.8, 122.6, 125.7, 130.3, 142.3, 159.7, 187.9.

Provenance & Evidence