(3-Methoxy-4-nitro-phenyl)-(3,4,5-trimethoxy-phenyl)-methanol → (3-Methoxy-4-nitro-phenyl)-(3,4,5-trimethoxy-phenyl)-methanone

HRID 971002Notes

Reaction equation

HRID 971002 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])[C:17]([O:22][CH3:23])=[C:16]([O:24][CH3:25])[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])[C:17]([O:22][CH3:23])=[C:16]([O:24][CH3:25])[CH:15]=2)=[O:13])[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10]

Participants

4

Reactant 1

HCID 69203794(3-Methoxy-4-nitro-phenyl)-(3,4,5-trimethoxy-phenyl)-methanol

Product 1

HCID 69205076(3-Methoxy-4-nitro-phenyl)-(3,4,5-trimethoxy-phenyl)-methanoneYield 48%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

A suspension of (3-methoxy-4-nitro-phenyl)-(3,4,5-trimethoxy-phenyl)-methanol (2.1 g, 6.1 mmol) and MnO2 (6.0 g, 69 mmol) in CH2Cl2 (100 mL) was stirred at room temperature for 2 days. The mixture was filtered through Celite and the filtrate was concentrated. The crude product was purified by flash chromatography (silica gel, Hexane:EtOAc 7:3) to afford (3-methoxy-4-nitro-phenyl)-(3,4,5-trimethoxy-phenyl)-methanone (1.0 g, 48%): 1H NMR (CDCl3) δ 7.90 (d, J=8 Hz, 1H), 7.50 (d, J=0 Hz, 1H), 7.37 (d, J=6 Hz, 1H), 7.05 (s, 2H), 4.02 (s, 3H), 3.96 (s, 3H), 3.88 (s, 6H).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated
  3. customThe crude product was purified by flash chromatography (silica gel, Hexane:EtOAc 7:3)

Sources & evidence

ORD record
ord-25b5a477ead141ed9bec7799f12100a0
Source dataset
uspto-grants-2007_12
Patent number
US07312241B2

Reaction notes

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