Reaktion #77933

ord-1d5db7b87ba04ab28e678aade299c1eb

Reaktionsgleichung

[Na+].[OH-]
sodium hydroxide
C=CC#N
acrylonitrile
Cc1ccccc1[N+](=O)[O-]
ortho-nitrotoluene
C=CC#N
acrylonitrile
N#CCCCc1ccccc1[N+](=O)[O-]
4-(2-nitro-phenyl)butyronitrile
Ausbeute 40.0%

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Temperaturreflux condenser
  2. 2
    workup.ADDITIONis added dropwise
  3. 3
    Temperaturmaintained at this temperature for 3 h
  4. 4
    SonstigeThe phases are separated
  5. 5
    Sonstigethe organic phase is dried
  6. 6
    Filtrationfiltered off

Vorschrift

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.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06706924B2uspto-grants-2004_03