2-Nitropropane → 4-Methyl-4-nitrovaleronitrile

HRID 1744028Notes

Reaction equation

HRID 1744028 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-0ef10877582c4bdab499913352680583
Source dataset
uspto-grants-2006_03
Patent number
US07012152B2

Reaction notes

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