(3-Methoxy-4-nitro-phenyl)-(3,4-dimethoxy-phenyl)-methanol → (3-Methoxy-4-nitro-phenyl)-(3,4-dimethoxy-phenyl)-methanone
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH3:23])[CH:15]=2)[OH:13])[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10]>C(Cl)Cl.O=[Mn]=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH3:23])[CH:15]=2)=[O:13])[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10]Participants
4
Procedure
A suspension of (3-methoxy-4-nitro-phenyl)-(3,4-dimethoxy-phenyl)-methanol (1.9 g, 6.0 mmol) and MnO2 (9.1 g, 104.7 mmol) in CH2Cl2 (100 mL) was stirred for 2 days. The mixture was filtered through Celite and the Celite was washed with CH2Cl2. The filtrate was concentrated and the residue was purified by flash chromatography (silica gel, CH2Cl2:EtOAc 95:5) to afford (3-methoxy-4-nitro-phenyl)-(3,4-dimethoxy-phenyl)-methanone (1.2 g, 64%) of yellow solid: 1H NMR (CDCl3) δ 7.87 (d, J=8 Hz, 1H), 7.50-7.46 (dd, J=2, 5.7 Hz, 2H), 7.36-7.30 (m, 2H), 6.93 (d, J=8 Hz, 1H), 4.01 (s, 3H), 3.98 (s, 3H), 3.96 (s, 3H).