3,5-Dimethoxy-a-(3-methoxyphenyl)benzenemethanol → (3,5-Dimethoxyphenyl)-(3-methoxyphenyl)methanone

HRID 971015Notes

Reaction equation

HRID 971015 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=2)[OH:12])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1>C(Cl)Cl.O=[Mn]=O>[CH3:10][O:9][C:7]1[CH:6]=[C:5]([C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=2)=[O:12])[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=1

Participants

4

Reactant 1

HCID 638952883,5-Dimethoxy-a-(3-methoxyphenyl)benzenemethanol

Product 1

HCID 69203980(3,5-Dimethoxyphenyl)-(3-methoxyphenyl)methanone

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (3,5-dimethoxyphenyl)-(3-methoxyphenyl)methanol (2.47 g, 9.0 mmol) in CH2Cl2 (20 ml) at rt was added activated MnO2 powder (3.91 g, 45 mmol) and kept adding 2˜3 equivalents of MnO2 every 3˜5 h until HPLC showed at least 98% conversion occurred. The black suspension was filtered through a Celite pad, concentrated in vacuo to give (3,5-dimethoxy-phenyl)-(3-methoxy-phenyl)methanone was an oil (2.35 g, 92%): 1HNMR (CDCl3) δ 7.38-7.35 (m, 3H, Ar), 7.15-7.13 (m, 1H, Ar), 6.93 (d, J=2 Hz, 2H, Ar), 6.67 (t, J=2 Hz, 1H, Ar), 3.86 (s, 3H, single OCH3 group), 3.83 (s, 6H, 2OCH3), 0.99 (s, 9H, 3OCH3). The product was carried over to the next step.

Workup

  1. filtrationThe black suspension was filtered through a Celite pad
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2d63d4b89b154261a07699c370f9ca42
Source dataset
uspto-grants-2007_12
Patent number
US07312241B2

Reaction notes

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