Nitromethane → 2-Methyl-4-(2-nitrovinyl)phenol

反応式

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

参加物

実験手順

Dissolve 2-methyl-4-hydroxy-benzaldehyde (980 mg, 6.3 mmol), nitromethane (2.0 mL, 37.7 mmol) and ammonium acetate (1.9 g, 25.1 mmol) in acetic acid (9 mL). Heat eh reaction mixture at 110° C. for 2 hours. Concentrate the reaction mixture under reduced pressure and partition the residue between ether and water. Separate the layers and dry with Na2SO4, filter and concentrate under reduced pressure to afford a crude product. Purify the crude by flash chromatography (eluent: EtOAc/hexane 20/80 and 30/70) to afford the title compound (1.0 g). 1H-NMR (CDCl3, 200 MHz): 7.94 (d, 1H, J=13.4 Hz), 7.50 (d, 1H, J=13.6 Hz), 7.34-7.27 (m, 2H), 6.82 (d, 1H, J=8.1 Hz), 2.28 (s, 3H).