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

HRID 2378247Notes

Reaction equation

HRID 2378247 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-eaade7f64eac4ab980feebc8e53c8c66
Source dataset
uspto-grants-2008_12
Patent number
US07470723B2

Reaction notes

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