HCID 69204493, compound → (3-Benzyloxyphenyl)-(3,5-dimethoxyphenyl)methanone

HRID 2378320Notes

Reaction equation

HRID 2378320 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]([C:17]2[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=[C:19]([O:25][CH3:26])[CH:18]=2)[OH:16])[CH:12]=[CH:13][CH:14]=1)[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:15]([C:17]2[CH:18]=[C:19]([O:25][CH3:26])[CH:20]=[C:21]([O:23][CH3:24])[CH:22]=2)=[O:16])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 69204493HCID 69204493, compound

Product 1

HCID 69203059(3-Benzyloxyphenyl)-(3,5-dimethoxyphenyl)methanoneYield 93.1%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (3-benzyloxy-phenyl)-(3,5-dimethoxy-phenyl)-methanol (11.51 g, 32.9 mmol) in CH2Cl2 (30 mL) at room temperature was added activated MnO2 powder (13.28 g, 153 mmol) and kept adding 2˜3 equivalents of MnO2 every 3˜5 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-phenyl)-(3,5-dimethoxy-phenyl)-methanone as a clear oil (10.67 g, 93% yield): 1H NMR (CDCl3) δ 3.82 (s, 6H, OCH3), 5.11 (s, 2H, CH2), 6.67 (t, J=2 Hz, 1H, Ar), 6.92 (d, J=2 Hz, 2H, Ar), 7.17-7.22 (m, 1H, Ar), 7.33-7.45 (m, 8H, 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-75cab3d8fe4b4749b6f9337804f5df78
Source dataset
uspto-grants-2008_12
Patent number
US07470723B2

Reaction notes

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