(3-Ethoxy-4-methoxy-phenyl)-(3-methoxy-phenyl)-methanol → HCID 69203654, compound

HRID 2378314Notes

Reaction equation

HRID 2378314 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:12]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[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][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=2)=[O:13])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH3:2]

Participants

4

Reactant 1

HCID 69205667(3-Ethoxy-4-methoxy-phenyl)-(3-methoxy-phenyl)-methanol

Product 1

HCID 69203654HCID 69203654, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (3-ethoxy-4-methoxy-phenyl)-(3-methoxy-phenyl) -methanol (1.75 g, 6.1 mmol) in CH2Cl2 (20 mL) at room temperature was added activated MnO2 powder (3.5 g, 40 mmol) and kept adding 23 equivalents of MnO2 every 35 h until HPLC showed disappearance of the starting material. The black suspension was filtered through a Celite pad, concentrated in vacuo to give (3-ethoxy-4-methoxy-phenyl)-(3-methoxy-phenyl)-methanone as an off-white solid (1.60 g, 92% yield): 1H NMR (CDCl3) δ 1.53 (t, J=7 Hz, 3H, CH2CH3), 3.86 (s, 3H, OCH3), 3.96 (s, 3H, OCH3), 4.17 (q, J=7 Hz, 2H, CH2CH3), 6.90 (d, J=8 Hz, 1H, Ar), 7.09-7.14 (m, 1H, Ar), 7.29-7.49 (m, 5H, Ar). The product was used in the next step without further purification.

Workup

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

Sources & evidence

ORD record
ord-82438441b9aa4e4c9e4e60044b4120a3
Source dataset
uspto-grants-2008_12
Patent number
US07470723B2

Reaction notes

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