2-Nitrotoluene → 4-(2-Nitrophenyl)butyronitrile

HRID 49655

Reaction equation

HRID 49655 reaction equation
[OH-].[Na+].[C:3](#[N:6])[CH:4]=[CH2:5].[N+:7]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH3:16])([O-:9])=[O:8]>[Cl-].C([N+](CCCC)(CCCC)C)CCC>[C:3](#[N:6])[CH:4]=[CH2:5].[N+:7]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH2:16][CH2:5][CH2:4][C:3]#[N:6])([O-:9])=[O:8]

Participants

6

Reactant 3

HCID 69442-NitrotolueneHCID 7855AcrylonitrileHCID 14798Sodium Hydroxide

Product 2

HCID 7855AcrylonitrileHCID 112177214-(2-Nitrophenyl)butyronitrileYield 40%

Reagents, catalysts & solvents 1

HCID 91822Tributylmethylammonium chlorideCatalyst

Procedure

0.75 ml of 45% sodium hydroxide solution and 175 mg of tributylmethylammonium chloride are placed in a 100 ml three-neck flask with a dropping funnel, reflux condenser and internal thermometer, stirring. At 40° C., a mixture of 1.4 ml acrylonitrile (21.15 mmol) and 25 ml ortho-nitrotoluene is added dropwise and maintained at this temperature for 3 h. The phases are separated, and the organic phase is dried and filtered off. With quantitative conversion of acrylonitrile, 1.61 g of 4-(2-nitro-phenyl)butyronitrile (8.5 mmol, 40%) are obtained.

Workup

  1. temperaturereflux condenser
  2. additionis added dropwise
  3. temperaturemaintained at this temperature for 3 h
  4. customThe phases are separated
  5. customthe organic phase is dried
  6. filtrationfiltered off

Sources & evidence

ORD record
ord-1d5db7b87ba04ab28e678aade299c1eb
Source dataset
uspto-grants-2004_03
Patent number
US06706924B2

Linked notes

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