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

HRID 2378200Notes

Reaction equation

HRID 2378200 reaction equation
COC1C=CC(C(C2C=CC(OC)=C(OC)C=2)=O)=CC=1[N+]([O-])=O.[CH3:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([CH:32]([C:34]2[CH:39]=[C:38]([O:40][CH3:41])[C:37]([O:42][CH3:43])=[C:36]([O:44][CH3:45])[CH:35]=2)[OH:33])=[CH:28][C:27]=1[N+:46]([O-:48])=[O:47].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>>[CH3:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]([C:34]2[CH:35]=[C:36]([O:44][CH3:45])[C:37]([O:42][CH3:43])=[C:38]([O:40][CH3:41])[CH:39]=2)=[O:33])=[CH:28][C:27]=1[N+:46]([O-:48])=[O:47]

Participants

4

Reactant 3

HCID 69203242(4-Methoxy-3-nitro-phenyl)-(3,4-dimethoxy-phenyl)-methanoneHCID 69203883(4-Methoxy-3-nitro-phenyl)-(3,4,5-trimethoxy-phenyl)-methanolHCID 178418287HCID 178418287, compound

Product 1

HCID 12137087(4-Methoxy-3-nitro-phenyl)-(3,4,5-trimethoxy-phenyl)-methanoneYield 55%

Procedure

(4-Methoxy-3-nitro-phenyl)-(3,4,5-trimethoxy-phenyl)-methanone was prepared analogously to (4-methoxy-3-nitro-phenyl)-(3,4-dimethoxy-phenyl)-methanone using (4-methoxy-3-nitro-phenyl)-(3,4,5-trimethoxy-phenyl)-methanol (2.4 g, 6.9 mmol) and pyridinium chlorochromate (2.2 g, 10.3 mmol). The crude product was purified by flash chromatography (silica gel, CH2Cl2:EtOAc 95:5) to afford (4-methoxy-3-nitro-phenyl)-(3,4,5-trimethoxy-phenyl)-methanone (1.3 g, 55%) as a white solid: 1H NMR (CDCl3) δ 8.34 (d, J=2 Hz, 1H), 8.10-8.06 (dd, J=2, 8 Hz, 1H), 7.22 (d, J=8 Hz, 1H), 7.01 (s, 2H), 4.07 (s, 3H), 3.95 (s, 3H), 3.87 (s, 3H).

Workup

  1. customThe crude product was purified by flash chromatography (silica gel, CH2Cl2:EtOAc 95:5)

Sources & evidence

ORD record
ord-157b8d1ab11e4d77b420dec2f7ea7547
Source dataset
uspto-grants-2008_12
Patent number
US07470723B2

Reaction notes

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