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

HRID 1079413ノート

反応式

HRID 1079413 の反応式
[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

参加物

4

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 14801Manganese dioxide触媒3 回HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-f8c78e8617104ec081e92b0a10620beb
出典データセット
uspto-grants-1996_12
特許番号
US05580888

反応ノート

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