Methyl vinyl ketone → HCID 54012949, Verbindung

HRID 1029946Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1029946
[CH3:1][C:2](=[O:5])[CH:3]=[CH2:4].[Cl:6][C:7]1[CH:8]=[C:9]([CH:13]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=2)[CH:14]=O)[CH:10]=[CH:11][CH:12]=1.[OH-].[K+]>C(OCC)C.C(O)C.C(OCC)(=O)C.O>[Cl:6][C:7]1[CH:8]=[C:9]([C:13]2([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=3)[CH2:14][CH2:1][C:2](=[O:5])[CH:3]=[CH:4]2)[CH:10]=[CH:11][CH:12]=1

Komponenten

8

Edukt 3

HCID 6570Methyl vinyl ketoneHCID 14797Potassium HydroxideHCID 54374521HCID 54374521, Verbindung

Produkt 1

HCID 54012949HCID 54012949, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Butenone (11.3 cc) is added to a solution of bis-(3-chlorophenyl)acetaldehyde (36.9 g) in ethyl ether (200 cc) and then, after cooling to 0° C., a solution of potassium hydroxide (3.1 g) in ethanol (20 cc) is added dropwise. The reaction mixture is stirred for 2 h at 0° C. and then for 16 hours at 25° C. and diluted with ethyl acetate (100 cc) and water (200 cc). The aqueous phase is washed with ethyl acetate (100 cc). The combined organic phases are washed with saturated sodium chloride solution (3×100 cc), dried over magnesium sulphate and concentrated under reduced pressure (2.7 kPa). The residue is chromatographed on a silica gel column (particle size 0.04-0.063 mm, diameter 7 cm, height 42 cm), eluting under a nitrogen pressure of 0.5 bar with a mixture of cyclohexane and ethyl acetate (90/10 by volume). 4,4-bis-(3-Chlorophenyl)cyclohexenone (27.7 g) is obtained in the form of yellow oil.

Aufarbeitung

  1. waitfor 16 hours at 25° C.
  2. washThe aqueous phase is washed with ethyl acetate (100 cc)
  3. washThe combined organic phases are washed with saturated sodium chloride solution (3×100 cc)
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated under reduced pressure (2.7 kPa)
  6. customThe residue is chromatographed on a silica gel column (particle size 0.04-0.063 mm, diameter 7 cm, height 42 cm)
  7. washeluting under a nitrogen pressure of 0.5 bar
  8. additionwith a mixture of cyclohexane and ethyl acetate (90/10 by volume)

Quellen und Nachweise

ORD-Eintrag
ord-13b6ec5d68e34b7f97b70a3c840d10b0
Quelldatensatz
uspto-grants-1992_04
Patentnummer
US05102667

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