(5-Methoxy-2-nitro-phenyl)-(3,4,5-trimethoxy-phenyl)-methanol → (5-Methoxy-2-nitro-phenyl)-(3,4,5-trimethoxy-phenyl)-methanone

HRID 2378202Notes

Reaction equation

HRID 2378202 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:27]=[CH:28][C:29]([N+:46]([O-:48])=[O:47])=[C:30]([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:31]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>>[CH3:24][O:25][C:26]1[CH:27]=[CH:28][C:29]([N+:46]([O-:48])=[O:47])=[C:30]([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:31]=1

Participants

4

Reactant 3

HCID 11783038(5-Methoxy-2-nitro-phenyl)-(3,4,5-trimethoxy-phenyl)-methanolHCID 69203242(4-Methoxy-3-nitro-phenyl)-(3,4-dimethoxy-phenyl)-methanoneHCID 178418287HCID 178418287, compound

Product 1

HCID 11089313(5-Methoxy-2-nitro-phenyl)-(3,4,5-trimethoxy-phenyl)-methanoneYield 77.2%

Procedure

(5-Methoxy-2-nitro-phenyl)-(3,4,5-trimethoxy-phenyl)-methanone was prepared analogously to (4-methoxy-3-nitro-phenyl)-(3,4-dimethoxy-phenyl)-methanone using (5-methoxy-2-nitro-phenyl)-(3,4,5-trimethoxy-phenyl)-methanol (2.9 g, 8.2 mmol) and pyridinium chlorochromate (2.6 g, 12.2 mmol). The crude product was purified by flash chromatography (silica gel, CH2Cl2:EtOAc 95:5) to afford (5-methoxy-2-nitro-phenyl)-(3,4,5-trimethoxy-phenyl)-methanone (2.2 g, 76%) as a white solid: 1H NMR (CDCl3) δ 8.22 (d, J=9 Hz, 1H), 7.11-7.06 (dd, J=3, 9 Hz, 1H), 7.00 (s, 2H), 6.89 (d, J=2 Hz, 1H), 3.93 (s, 3H), 3.92 (s, 3H), 3.82 (s, 6H); 13C NMR (CDCl3) δ 191.95, 164.01, 153.25, 143.37, 139.57, 138.57, 130.85, 126.93, 115.30, 113.49, 106.78, 60.93, 56.32, 56.25.

Workup

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

Sources & evidence

ORD record
ord-5dacbb1b0af745548a418cad377413de
Source dataset
uspto-grants-2008_12
Patent number
US07470723B2

Reaction notes

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