Water → 1,5-Bis(4-acetoxyphenyl)-1,4-pentadien-3-one

Participants

Reaction Steps

1,5-Bis(4-hydroxyphenyl)-1,4-pentadien-3-one (20f, 0.26 g, 1.0 mmol) was dissolved in acetic anhydride (21, 7.00 ml, 74.1 mmol) and stirred for 5 min at room temperature. Pyridine (0.70 ml, 8.7 mmol) was added and the mixture stirred for 30 min at 100° C. The resulting mixture was poured into water, extracted with ethyl acetate, washed with saturated sodium chloride, dried over magnesium sulfate, filtered and evaporated to afford a solid. The crude solid was recrystallized from tetrahydrofuran/hexane to give 0.28 g (82%) of a yellow solid: mp 167-168° C. [expected mp 167-168° C.]; 1H NMR: δ 2.30 (s, 6H), 7.00 (d, 2H, J=15.9 Hz), 7.13 (d, 4H, J=8.3 Hz), 7.60 (d, 4H, J=8.2 Hz), 7.69 (d, 2H, J=15.9 Hz); 13C NMR: δ 21.1, 122.1, 125.4, 129.4, 132.4, 142.1, 152.2, 168.9, 188.3; Exact mass calcd for C21H18O5: 350.1154, observed (M+H) 351.1232.

Provenance & Evidence