Nitromethane → 5-Methoxy-2-(2-nitroethenyl)phenol

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[OH:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:3]=1[CH:4]=O.[N+:12]([CH3:15])([O-:14])=[O:13].C([O-])(=O)C.[NH4+]>C(O)(=O)C>[CH3:11][O:10][C:8]1[CH:7]=[CH:6][C:3](/[CH:4]=[CH:15]/[N+:12]([O-:14])=[O:13])=[C:2]([OH:1])[CH:9]=1

참가 물질

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온도: 100 °C

실험 절차

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).