4-Hydroxybenzaldehyde → HCID 88582986, compound

Participants

Reaction Steps

To a stirring solution of (4-{[(2Z)-2-(methoxyimino)-2-phenylethyl]oxy}phenyl)methanol (10 g, 37 mmol) and 4-hydroxybenzaldehyde (4.5 g, 37 mmol) in THF (100 mL) was added triphenylphosphine (12.2 g, 46.5 mmol) and Diisopropyl azodicarboxylate (11.2 g, 55 mmol) at 0° C., then stirred at RT for 12 h. RM diluted with water and extracted with ethyl acetate. The organic layer was washed with brine solution, dried over Na2SO4 and concentrated to pale brown oil. Crude was purified by column (100-200 silica) using 8% ethyl acetate to get the titled compound as white solid (5 g, Yield: 36.2%). 1H NMR (300 MHz, CDCl3): δ 9.81 (s, 1H), 7.74-7.77 (d, 2H), 7.58-7.61 (m, 2H), 7.24-7.29 (m, 5H), 6.97-6.99 (d, 2H), 6.85-6.87 (d, 2H), 5.13 (s, 2H), 4.98 (s, 2H), 3.98 (s, 3H).

Provenance & Evidence