(3-Methoxy-4-nitro-phenyl)-(3,4-dimethoxy-phenyl)-methanol → (3-Methoxy-4-nitro-phenyl)-(3,4-dimethoxy-phenyl)-methanone

HRID 971039Notes

Reaction equation

HRID 971039 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

Reactant 1

HCID 69205180(3-Methoxy-4-nitro-phenyl)-(3,4-dimethoxy-phenyl)-methanol

Product 1

HCID 69205611(3-Methoxy-4-nitro-phenyl)-(3,4-dimethoxy-phenyl)-methanoneYield 64%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

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).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. washthe Celite was washed with CH2Cl2
  3. concentrationThe filtrate was concentrated
  4. customthe residue was purified by flash chromatography (silica gel, CH2Cl2:EtOAc 95:5)

Sources & evidence

ORD record
ord-407a4bea07664ea7a7bec39dac02b3ce
Source dataset
uspto-grants-2007_12
Patent number
US07312241B2

Reaction notes

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