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

HRID 54592ノート

反応式

HRID 54592 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 10h and the mixture stirred for 18 h, then filtered through Celite® and concentrated in vacuo. The residue was recrystallized 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. filtrationfiltered through Celite®
  3. concentrationconcentrated in vacuo
  4. customThe residue was recrystallized from EtOH

出典と根拠

ORDレコード
ord-ce20b3d35aa9447d8950bbbac84e1741
出典データセット
uspto-grants-1997_04
特許番号
US05622977

反応ノート

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