Desoxyanisoin → 1,2-Bis(4-hydroxyphenyl)ethanone

Participants

Reaction Conditions

Reaction Steps

Desoxyanisoin (5.00 g, 19.5 mmol) and pyridine hydrochloride (9.02 g, 78.0 mmol) were added to a round-bottom flask equipped with a condenser. The mixture was refluxed for 5 h at 200° C., cooled to room temperature, and poured into water. The precipitate was filtered and recrystallized from acetic acid to give 3.8 g (85% yield) of a pale yellow crystalline solid. 1H NMR (DMSO-d4, 300 MHz, ppm): 10.35 (s, 1H, HO—Ar—CO), 9.28 (s, 1H, HO—Ar—CH2), 7.91 (d, 2H, J=8.7 Hz, Ar—H), 7.04 (d, 2H, J=8.5 Hz, Ar—H), 6.84 (d, 2H, J=8.7 Hz, Ar—H), 6.68 (d, 2H, J=8.5 Hz, Ar—H), 4.11 (s, 2H, Ar—CO—CH2—Ar). 13C NMR (DMSO-d6, 75 MHz, ppm): 196.5, 162.3, 156.2, 131.3, 130.7, 128.1, 125.9, 115.5, 115.4, 43.7.

Provenance & Evidence