(3,5-Dimethoxy-phenyl)-(4-methoxy-3-nitro-phenyl)-methanol → (3,5-Dimethoxy-phenyl)-(4-methoxy-3-nitro-phenyl)-methanone

HRID 2378205Notes

Reaction equation

HRID 2378205 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])[CH:37]=[C:36]([O:42][CH3:43])[CH:35]=2)[OH:33])=[CH:28][C:27]=1[N+:44]([O-:46])=[O:45].[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:39]=[C:38]([O:40][CH3:41])[CH:37]=[C:36]([O:42][CH3:43])[CH:35]=2)=[O:33])=[CH:28][C:27]=1[N+:44]([O-:46])=[O:45]

Participants

4

Reactant 3

HCID 69202587(3,5-Dimethoxy-phenyl)-(4-methoxy-3-nitro-phenyl)-methanolHCID 69203242(4-Methoxy-3-nitro-phenyl)-(3,4-dimethoxy-phenyl)-methanoneHCID 178418287HCID 178418287, compound

Product 1

HCID 69203253(3,5-Dimethoxy-phenyl)-(4-methoxy-3-nitro-phenyl)-methanoneYield 82.2%

Procedure

(4-Methoxy-3-nitro-phenyl)-(3,5-dimethoxy-phenyl)-methanone was prepared analogously to (4-methoxy-3-nitro-phenyl)-(3,4-dimethoxy-phenyl)-methanone using (4-methoxy-3-nitro-phenyl)-(3,5-dimethoxy-phenyl)-methanol (3.7 g, 11.5 mmol) and pyridinium chlorochromate (3.7 g, 17.0 mmol). The crude product was purified by flash chromatography (silica gel, CH2Cl2:EtOAc 9:1) to afford (4-methoxy-3-nitro-phenyl)-(3,5-dimethoxy-phenyl)-methanone (3.0 g, 82%) as a white solid: 1H NMR (CDCl3) δ 8.33 (d, J=2 Hz, 1H), 8.09 (d, J=9.1 Ha, 1H), 7.20-7.15 (dd, J=3, 8 Hz, 1H), 6.84 (d, J=2 Hz, 2H), 6.69 (m, 1H), 4.06 (s, 3H), 3.83 (s, 6H).

Workup

  1. customThe crude product was purified by flash chromatography (silica gel, CH2Cl2:EtOAc 9:1)

Sources & evidence

ORD record
ord-2c0425d87019459588955e260546239e
Source dataset
uspto-grants-2008_12
Patent number
US07470723B2

Reaction notes

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