HCID 69202543, compound → (3-Methoxy-4-nitro-phenyl)-(3,5-dimethoxy-phenyl)-methanone

HRID 2378249Notes

Reaction equation

HRID 2378249 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:12]([C:14]2[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[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]=[C:18]([O:20][CH3:21])[CH:17]=[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 69202543HCID 69202543, compound

Product 1

HCID 69202533(3-Methoxy-4-nitro-phenyl)-(3,5-dimethoxy-phenyl)-methanoneYield 94.8%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

A suspension of (3-methoxy-4-nitro-phenyl)-(3,5-dimethoxy-phenyl)-methanol (3.9 g, 12.3 mmol) and MnO2 (8.5 g, 98.4 mmol) in CH2Cl2 (100 mL) was stirred for 3 days. The mixture was filtered through Celite and the Celite was washed with CH2Cl2. The filtrate was concentrated to afford (3-methoxy-4-nitro-phenyl)-(3,5-dimethoxy-phenyl)-methanone (3.7 g, 94%): 1H NMR (CDCl3) δ 7.85 (d, J=8 Hz, 1H), 7.52 (d, J=0.9 Hz, 1H), 7.39-7.35 (dd, J=2, 9.6 Hz, 1H), 6.89 (d, J=2 Hz, 2H), 6.71 (d, J=2 Hz, 1H), 4.01 (s, 3H), 3.83 (s, 6H).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. washthe Celite was washed with CH2Cl2
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-5f991506e863441aa16eab53d91c0033
Source dataset
uspto-grants-2008_12
Patent number
US07470723B2

Reaction notes

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