2-Nitropropane → 4-Methyl-4-nitrovaleronitrile

HRID 433000Notes

Reaction equation

HRID 433000 reaction equation
[C:1](#[N:4])[CH:2]=[CH2:3].[N+:5]([CH:8]([CH3:10])[CH3:9])([O-:7])=[O:6]>[Cl-].C([N+](C)(C)C)CCCCCCCCCCCCCCC.[OH-].[Na+]>[CH3:9][C:8]([N+:5]([O-:7])=[O:6])([CH3:10])[CH2:3][CH2:2][C:1]#[N:4]

Participants

5

Reactant 2

HCID 3982-NitropropaneHCID 7855Acrylonitrile

Product 1

HCID 38791404-Methyl-4-nitrovaleronitrileYield 64.6%

Reagents, catalysts & solvents 2

HCID 8154Hexadecyltrimethylammonium chlorideCatalystHCID 14798Sodium HydroxideSolvent

Procedure

Acrylonitrile (6.0 g, 113 mmol), 2-nitropropane (12.0 g, 135 mmol) and hexadecyltrimethyl ammonium chloride (2.0 g) were stirred in a 0.1N aqueous sodium hydroxide solution (200 ml) overnight at room temperature. The layers were separated and the aqueous layer was extracted twice with methylene chloride (50 ml). The combined organic layer was washed with saturated brine (30 ml). The solvent was evaporated and the residue was dried to give oily 4-methyl-4-nitrovaleronitrile (10.4 g, 73 mmol, yield 64.6%).

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted twice with methylene chloride (50 ml)
  3. washThe combined organic layer was washed with saturated brine (30 ml)
  4. customThe solvent was evaporated
  5. customthe residue was dried

Sources & evidence

ORD record
ord-2b31a6a9f5244fc6b70accd89a114f91
Source dataset
uspto-grants-2003_12
Patent number
US06664412B2

Reaction notes

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