Potassium Cyanide → 3-Oxo-1-phenylcyclohexanecarbonitrile

HRID 11213

반응식

HRID 11213 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

HCID 123391223-Oxo-1-phenylcyclohexanecarbonitrile수율 92%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
93 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-252ad776d6b649efaee5e0abcd5fe44a
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07098203B2

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