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

HRID 54592Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 54592
[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

Komponenten

4

Edukt 1

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

Produkt 1

HCID 10827779(3-Cyclopentyloxy-4-methoxy-phenyl)-phenyl-methanoneAusbeute 84,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 14801Manganese dioxideKatalysator3×HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-ce20b3d35aa9447d8950bbbac84e1741
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05622977

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