2-Nitropropane → 4-Methyl-4-nitrovaleronitrile

HRID 858968Notes

Reaction equation

HRID 858968 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-5876e68781f543829c661004d2c4b3bc
Source dataset
uspto-grants-2006_12
Patent number
US07148371B2

Reaction notes

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