Potassium Cyanide → 2-(Propan-2-yl)butanedinitrile

HRID 880421Notes

Reaction equation

HRID 880421 reaction equation
[C-:1]#[N:2].[K+].[C:4]([C:6](=[CH:12][CH:13]([CH3:15])[CH3:14])C(OCC)=O)#[N:5]>O.C(O)C>[CH:13]([CH:12]([CH2:6][C:4]#[N:5])[C:1]#[N:2])([CH3:14])[CH3:15]

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 54168338HCID 54168338, compound

Product 1

HCID 1368682-(Propan-2-yl)butanedinitrileYield 74%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of potassium cyanide (5.81 g, 89.52 mmol) in water (12 mL) was added to a solution of ethyl 2-cyano-4-methyl-pent-2-enoate (6.5 g, 38.92 mmol) in ethanol (20 mL) at room temperature and the reaction mixture was stirred overnight. The resulting mixture was refluxed for 2 h and then cooled to room temperature. The ethanol was evaporated and the residue dissolved in dichloromethane. The dichloromethane layer was washed with water and brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 2-isopropylbutanedinitrile (3.5 g, 74%) as a liquid.

Workup

  1. temperatureThe resulting mixture was refluxed for 2 h
  2. customThe ethanol was evaporated
  3. dissolutionthe residue dissolved in dichloromethane
  4. washThe dichloromethane layer was washed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b613ab7d7e274f93bf3ca0d5c5e81b17
Source dataset
uspto-grants-2015_03
Patent number
US08993574B2

Reaction notes

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