Water → (4-(4-Methyl-3-pentenyl)-3-cyclohexenyl)acetonitrile

HRID 2227098Notes

Reaction equation

HRID 2227098 reaction equation
S([C:5]1[CH:11]=[CH:10][C:8]([CH3:9])=[CH:7][CH:6]=1)([O-])(=O)=O.[C-:12]#[N:13].[K+].O>CS(C)=O>[CH3:9][C:8]([CH3:10])=[CH:7][CH2:6][CH2:5][C:5]1[CH2:11][CH2:10][CH:8]([CH2:9][C:12]#[N:13])[CH2:7][CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 9032Potassium CyanideHCID 85570p-Toluenesulfonate

Product 1

HCID 18471789(4-(4-Methyl-3-pentenyl)-3-cyclohexenyl)acetonitrile

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of tosylate 1H (R=4-Methyl-3-pentenyl) (20 g) in dimethylsulfoxide (178 mL) is added potassium cyanide (19.4 g). The reaction mixture is heated to 100° C., and the reaction mixture is stirred at that temperature for three hours. The reaction mixture is cooled to room temperature, added to water (300 mL), and extracted with hexane. The combined organic layers are dried over magnesium sulfate and the solution is concentrated in vacuo.

Workup

  1. temperatureThe reaction mixture is cooled to room temperature
  2. extractionextracted with hexane
  3. dry with materialThe combined organic layers are dried over magnesium sulfate
  4. concentrationthe solution is concentrated in vacuo

Sources & evidence

ORD record
ord-433844a784894642a04da8257ead6d84
Source dataset
uspto-grants-2002_07
Patent number
US06413448B1

Reaction notes

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