(3-Ethoxy-4-methoxy-phenyl)-(4-methoxy-3-nitro-phenyl)-methanol → (3-Ethoxy-4-methoxy-phenyl)-(4-methoxy-3-nitro-phenyl)-methanone

HRID 2378256Notes

Reaction equation

HRID 2378256 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([N+:22]([O-:24])=[O:23])[CH:15]=2)[OH:13])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH3:2]>C(Cl)Cl.O=[Mn]=O>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([N+:22]([O-:24])=[O:23])[CH:15]=2)=[O:13])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH3:2]

Participants

4

Reactant 1

HCID 69203000(3-Ethoxy-4-methoxy-phenyl)-(4-methoxy-3-nitro-phenyl)-methanol

Product 1

HCID 69204020(3-Ethoxy-4-methoxy-phenyl)-(4-methoxy-3-nitro-phenyl)-methanoneYield 73%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

MnO2 (18 g, 210 mmol, 5 equivalent) was added to a stirred solution of the crude (3-ethoxy-4-methoxy-phenyl)-(4-methoxy-3-nitro-phenyl)-methanol in CH2Cl2 (100 mL). The reaction mixture was stirred at room temperature for 2 days and MnO2 [6 equivalent (3×2 eq.)] was added during this period of time. The reaction mixture was then filtered through celite and washed with CH2Cl2 (3×60 mL). Removal of solvent from the filtrate and chromatography (Silica Gel) gave (3-ethoxy-4-methoxy-phenyl)-(4-methoxy-3-nitro-phenyl)-methanone as a solid (8.74 g, 73% yield): 1H NMR (CDCl3) δ 1.47-1.53 (t, J=7.1 Hz, 3H, CH3), 3.97 (s, 3H, OCH3), 4.06 (s, 3H, OCH3), 4.13-4.21 (q, J=6.9, 14.0 Hz, 2H, CH2), 6.91-6.94 (d, J=8.3 Hz, 1H, Ar), 7.17-7.21 (d, J=8.7 Hz, 1H, Ar), 7.30-7.35 (dd, J=2.1, 8.5 Hz, 1H, Ar), 7.42 (d, J=1.9 Hz, 1H, Ar), 8.03-8.07 (dd, J=2.3, 8.7 Hz, 1H, Ar), 8.29 (d, J=2.0 Hz, 1H, Ar).

Workup

  1. filtrationThe reaction mixture was then filtered through celite
  2. washwashed with CH2Cl2 (3×60 mL)
  3. customRemoval of solvent from the filtrate and chromatography (Silica Gel)

Sources & evidence

ORD record
ord-1e59a2ac482242b8af7619c27213b068
Source dataset
uspto-grants-2008_12
Patent number
US07470723B2

Reaction notes

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