反应详情

温度

100 °C

A mixture of 2-hydroxy-4-methoxybenzaldehyde (5.0 g, 32.9 mmol), nitromethane (5.5 g 90.0 mmol), ammonium acetate (6.9 g 90.0 mmol) and 40 mL of glacial acetic acid was heated at 100° C. for 4 hours. The reaction was then cooled, concentrated and partitioned between ethyl acetate and water. The organic extract was washed with 10% sodium bicarbonate solution, water, and brine and dried over sodium sulfate. The organic solution was concentrated and chromatographed on a silica gel column eluting with 1:4 ethyl acetate/hexane to afford the titled compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 3.78 (s, 3H) 6.49-6.55 (m, 2H) 7.65 (d, J=8.33 Hz, 1H) 8.00-8.06 (d, J=13.5 Hz, 1H) 8.13-8.19 (d, J=13.5 Hz 1H) 11.00 (s, 1H).

1. temperatureThe reaction was then cooled
2. concentrationconcentrated
3. custompartitioned between ethyl acetate and water
4. extractionThe organic extract
5. washwas washed with 10% sodium bicarbonate solution, water, and brine
6. dry with materialdried over sodium sulfate
7. concentrationThe organic solution was concentrated
8. customchromatographed on a silica gel column
9. washeluting with 1:4 ethyl acetate/hexane