Acrylonitrile → Propanenitrile, 3,3'-[oxybis(2,1-ethanediyloxy)]bis-

HRID 433850Notes

Reaction equation

HRID 433850 reaction equation
[OH-].[Na+].[CH2:3]([OH:9])[CH2:4][O:5][CH2:6][CH2:7][OH:8].[C:10](#[N:13])[CH:11]=[CH2:12]>ClCCl>[C:10]([CH2:11][CH2:12][O:9][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:12][CH2:11][C:10]#[N:13])#[N:13]

Participants

5

Reactant 3

HCID 7855AcrylonitrileHCID 8117Diethylene GlycolHCID 14798Sodium Hydroxide

Product 1

HCID 89693Propanenitrile, 3,3'-[oxybis(2,1-ethanediyloxy)]bis-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2% (w/v) sodium hydroxide (5 mL) and diethylene glycol (5.3 g, 50 mmol) was added acrylonitrile (7.95 g, 150 mmol). The mixture was stirred at room temperature overnight and additioned with 50 mL dichloromethane. The organic layer was washed 2× with brine and dried (MgSO4). The solvent was removed by rotary evaporation. The oily residue was treated with 200 proof ethanol, and the solvent was removed by rotary evaporation. This was repeated 2× to remove excess unreacted acrylonitrile. The product was used without further purification

Workup

  1. washThe organic layer was washed 2× with brine
  2. dry with materialdried (MgSO4)
  3. customThe solvent was removed by rotary evaporation
  4. additionThe oily residue was treated with 200 proof ethanol
  5. customthe solvent was removed by rotary evaporation
  6. customto remove excess unreacted acrylonitrile
  7. customThe product was used without further purification

Sources & evidence

ORD record
ord-8be238e465644d18831fd3fc7b3250f1
Source dataset
uspto-grants-2003_12
Patent number
US06670194B1

Reaction notes

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