Ethanol → HCID 22908542, Verbindung

HRID 1734392Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1734392
[CH2:1]1[O:21][C:4]2([CH2:9][CH2:8][C:7]([C:10]3[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=3)=[CH:6][CH2:5]2)[O:3][CH2:2]1.C(O)C.C(OCC)(=O)C>[H][H]>[CH2:2]1[O:3][C:4]2([CH2:5][CH2:6][CH:7]([C:10]3[CH:15]=[CH:14][C:13]([O:16][C:17]([F:18])([F:20])[F:19])=[CH:12][CH:11]=3)[CH2:8][CH2:9]2)[O:21][CH2:1]1

Komponenten

5

Edukt 3

HCID 702EthanolHCID 8857Ethyl AcetateHCID 22908554HCID 22908554, Verbindung

Produkt 1

HCID 22908542HCID 22908542, VerbindungAusbeute 99,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 178418361HCID 178418361, VerbindungLösungsmittel2×

Versuchsvorschrift

A mixture of (4-trifluoromethoxyphenyl)cyclohexen-4-one ethyleneketal (43.3 g, 0.144 mol), ethanol (200 ml), ethyl acetate (50 ml) and Pa-C (2 g) was stirred at room temperature for 10 hours in hydrogen atmosphere (at that time, hydrogen (3.59 l) was consumed), filtering off the catalyst from the reaction solution, distilling off the solvent under reduced pressure, to obtain 4-(4-trifluoromethoxyphenyl) cyclohexanone ethyleneketal (43.5 g) (m.p. 41.2° C.), adding thereto formic acid (250 ml), heating the mixture under reflux for 2.5 hours, feeding the reaction substance into water, extracting with a mixed solvent of toluene (400 ml) with ethyl acetate (100 ml), twice washing the resulting organic layer with water, drying over anhydrous MgSO4, filtering off anhydrous MgSO4, distilling off the solvent under reduced pressure and subjecting the resulting residue to column chromatography (silica gel, eluent: toluene), to obtain 4-(4-trifluoromethoxyphenyl)cyclohexanone (20.7 g). Yield: 47%.

Aufarbeitung

  1. customwas consumed),
  2. filtrationfiltering off the catalyst from the reaction solution
  3. distillationdistilling off the solvent under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-f706a3636a6a40eea2258628a8bbeb4c
Quelldatensatz
uspto-grants-1996_07
Patentnummer
US05534187

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