Sodium Chloride → 3-Methyl-2-(propan-2-yl)butanenitrile

HRID 1680802Notes

Reaction equation

HRID 1680802 reaction equation
C(OC(=O)[C:5]([CH:11]([CH3:13])[CH3:12])([CH:8]([CH3:10])[CH3:9])[C:6]#[N:7])C.O=P1(C)CCC=C1.[Cl-].[Na+]>O>[CH:8]([CH:5]([CH:11]([CH3:13])[CH3:12])[C:6]#[N:7])([CH3:10])[CH3:9]

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 701042,3-Dihydro-1-methyl-1H-phosphole 1-oxideHCID 12463390Ethyl 2-cyano-3-methyl-2-(propan-2-yl)butanoate

Product 1

HCID 136998413-Methyl-2-(propan-2-yl)butanenitrileYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

98.5 g (0.5 mol) of diisopropyl-cyanoacetic acid ethyl ester (prepared according to J. Chem. Soc., 1930, page 2,758), 300 ml of 1-oxo-1-methyl-phospholine, 31 g of sodium chloride and 22 g of water were heated to 160°-170° C. for 9 hours. After cooling, the mixture was diluted with 1,000 ml of water and extracted by shaking four times with 150 ml of petroleum ether each time. The combined petroleum ether phases were washed twice with 200 ml of water each time and dried with Na2SO4 and the petroleum ether was distilled off under normal pressure. The residual crude product was then purified by vacuum distillation. 53.2 g (85% of theory) of diisopropyl-acetonitrile of boiling point 60° C./14 mm Hg were obtained. Refractive index nD20 =1.4190.

Workup

  1. temperatureAfter cooling
  2. extractionextracted
  3. washThe combined petroleum ether phases were washed twice with 200 ml of water each time
  4. dry with materialdried with Na2SO4
  5. distillationthe petroleum ether was distilled off under normal pressure
  6. distillationThe residual crude product was then purified by vacuum distillation

Sources & evidence

ORD record
ord-ee14cb9738184ddc95bd4954af833349
Source dataset
uspto-grants-1981_06
Patent number
US04276225

Reaction notes

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