Dibenzylidene acetone → 1,5-Diphenylpentan-3-ol

HRID 847580Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 847580
[CH:1](=[CH:8][C:9]([CH:11]=[CH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>[Pd]>[C:13]1([CH2:12][CH2:11][C:9](=[O:10])[CH2:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[C:13]1([CH2:12][CH2:11][CH:9]([OH:10])[CH2:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Komponenten

5

Edukt 2

HCID 95417Dibenzylidene acetoneHCID 178418361HCID 178418361, Verbindung

Produkt 2

HCID 214961,5-Diphenylpentan-3-oneHCID 128385101,5-Diphenylpentan-3-olAusbeute 28 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 23938PalladiumKatalysator

Versuchsvorschrift

A mixture of 1.00 g (4.27 mmol) of dibenzylidene acetone and 0.15 g of 10% palladium on carbon in 150 ml of methyl cellusolve was shaken under 4 atm. of hydrogen for 2 h. The solution was filtered and concentrated in vacuo. Flash chromatography using 10-20% ethyl acetate in hexane gave 0.60 g (59%) of 1,5-diphenyl-3-pentanone (Rf 0.43, 20% ethyl acetate in hexane) as a colorless Oil and 0.29 g (28%) of 1,5-diphenyl-3-pentanol (Rf 0.36) as a white solid, m.p. 43°-5° C. 1,5-Diphenyl-3-pentanone: 1H NMR (CDCl3) δ 2.71 (t, J=7 Hz, 4H), 2.89 (t, J=7 Hz, 4H), 7.1-7.3 (m, 10H). Mass spectrum (M+NH4)+ 256.

Aufarbeitung

  1. filtrationThe solution was filtered
  2. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-8f8186b85ce241969a133c66397642d8
Quelldatensatz
uspto-grants-1992_08
Patentnummer
US05142056

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