alpha-(3-Cyclopentyloxy-4-methoxyphenyl)benzylalcohol → (3-Cyclopentyloxy-4-methoxy-phenyl)-phenyl-methanone

HRID 1079413Notes

Reaction equation

HRID 1079413 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[OH:16])[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1>C(Cl)Cl.O=[Mn]=O>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C:15]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)=[O:16])[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 1

HCID 10565992alpha-(3-Cyclopentyloxy-4-methoxyphenyl)benzylalcohol

Product 1

HCID 10827779(3-Cyclopentyloxy-4-methoxy-phenyl)-phenyl-methanoneYield 84.9%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalyst3×HCID 6344DichloromethaneSolvent

Procedure

The alcohol (prepared above) (13.4 g, 44.8 mmol) was dissolved in CH2Cl2 (150 ml) and treated with MnO2 (22 g). The reaction mixture was vigorously stirred at RT for 18 h then treated with a further portion of MnO2 (20 g). More MnO2 (20 g) was added after 10 h and the mixture stirred for 18 h then filtered through Celite® and concentrated in vacuo. The residue was recrystallised from EtOH to afford the title compound (11.27 g; two crops) as a white crystalline solid m.p. 59°-75° C.; δH (CDCl3) 1.5-2.1 (8H, br, m, (CH2)4), 3.88 (3H, s, OMe), 4.80 (1H, br m, OCHCH2), 6.83 (1H, d, J 8.5 Hz, ArH ortho to OMe), and 7.25-7.8 (7H, m, 2×ArH meta to OMe+C6H5); m/z 296 (M+ 11%), 229 (17), 228 (95), 152 (12), 151 (100), 105 (30), 77 (21), and 41 (10).

Workup

  1. stirringthe mixture stirred for 18 h
  2. filtrationthen filtered through Celite®
  3. concentrationconcentrated in vacuo
  4. customThe residue was recrystallised from EtOH

Sources & evidence

ORD record
ord-f8c78e8617104ec081e92b0a10620beb
Source dataset
uspto-grants-1996_12
Patent number
US05580888

Reaction notes

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