HCID 69203609, compound → HCID 69205956, compound

HRID 2378293Notes

Reaction equation

HRID 2378293 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:17]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH2:28][CH3:29])[CH:20]=2)[OH:18])[CH:12]=[CH:13][C:14]=1[O:15][CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(Cl)Cl.O=[Mn]=O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:17]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH2:28][CH3:29])[CH:20]=2)=[O:18])[CH:12]=[CH:13][C:14]=1[O:15][CH3:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 69203609HCID 69203609, compound

Product 1

HCID 69205956HCID 69205956, compoundYield 100.8%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (3-benzyloxy-4-methoxy-phenyl)-(3-ethoxy-4-methoxy-phenyl)-methanol (7.22 g, 18.3 mmol) in CH2Cl2 (40 mL) at room temperature was added activated MnO2 powder (4.6 g, 53 mmol) and kept adding 2˜3 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-benzyloxy-4-methoxy-phenyl)-(3-ethoxy-4-methoxy-phenyl)-methanone as a brown solid (7.24 g, 100% yield): 1H NMR (CDCl3) δ 1.49 (t, J=7 Hz, 3H, CH2CH3), 3.95 (s, 3H, OCH3), 3.97 (s, 3H, OCH3), 4.14 (q, J=7 Hz, 2H, CH2CH3), 5.20 (s, 2H, CH2), 6.83 (d, J=8 Hz, 1H, Ar), 6.94 (d, J=8 Hz, 1H, Ar), 7.23-7.47 (m, 9H, 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-126d74c3d30943e7a0b8fb00d56a64ed
Source dataset
uspto-grants-2008_12
Patent number
US07470723B2

Reaction notes

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