Potassium Cyanide → 3-Oxo-1-phenylcyclohexanecarbonitrile

HRID 11213

Reaktionsgleichung

Reaktionsgleichung von HRID 11213
[C:1]1([C:7]2[CH2:12][CH2:11][CH2:10][C:9](=[O:13])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C-]#N.[K+].Cl.[CH3:18][N:19](C)C.C(=O)(O)[O-].[Na+]>O.CN(C=O)C>[O:13]=[C:9]1[CH2:10][CH2:11][CH2:12][C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)([C:18]#[N:19])[CH2:8]1

Komponenten

7

Edukt 4

HCID 9032Potassium CyanideHCID 825672-Cyclohexen-1-one, 3-phenyl-HCID 516892Sodium BicarbonateHCID 10313079Trimethylamine Hydrochloride

Produkt 1

HCID 123391223-Oxo-1-phenylcyclohexanecarbonitrileAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
93 °C

Versuchsvorschrift

A mixture of 3-phenylcyclohex-2-enone (14.3 mmol), potassium cyanide (1.92 g) and trimethylamine hydrochloride (2.06 g, 21.5 mmol) in H2O (10 mL) and DMF (57 mL) was heated at 93° C. for 6 hr. After cooling down to room temperature, saturated sodium bicarbonate was added and the organic layer was separated. The aqueous layer was extracted with diethyl ether 3 times. The combined organic layers were washed with saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated under vacuum to get 2.62 g of the crude 3-oxo-1-phenylcyclohexanecarbonitrile which was directly taken to the next step without further purification.

Aufarbeitung

  1. temperatureAfter cooling down to room temperature
  2. customthe organic layer was separated
  3. extractionThe aqueous layer was extracted with diethyl ether 3 times
  4. washThe combined organic layers were washed with saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-252ad776d6b649efaee5e0abcd5fe44a
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07098203B2

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