Potassium Cyanide → 3-Oxo-1-phenylcyclohexanecarbonitrile

HRID 11213

反応式

HRID 11213 の反応式
[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

参加物

7

反応物 4

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

生成物 1

HCID 123391223-Oxo-1-phenylcyclohexanecarbonitrile収率 92%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
93 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-252ad776d6b649efaee5e0abcd5fe44a
出典データセット
uspto-grants-2006_08
特許番号
US07098203B2

関連ノート

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