Water → 3-(3-Nitro-phenyl)-acrylonitrile

HRID 1837515

Reaction equation

HRID 1837515 reaction equation
[C:1]([CH2:3]P(=O)(OCC)OCC)#[N:2].[H-].[Na+].[N+:14]([C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH:20]=O)([O-:16])=[O:15].O>O1CCCC1>[N+:14]([C:17]1[CH:18]=[C:19]([CH:20]=[CH:3][C:1]#[N:2])[CH:22]=[CH:23][CH:24]=1)([O-:16])=[O:15]

Participants

6

Reactant 4

HCID 962WaterHCID 74493-NitrobenzaldehydeHCID 24758Sodium hydrideHCID 75676Diethyl (cyanomethyl)phosphonate

Product 1

HCID 556693-(3-Nitro-phenyl)-acrylonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

At 0° C., 75.5 g of diethyl cyanomethylphosphonate dissolved in tetrahydrofuran are poured into a suspension of sodium hydride in tetrahydrofuran. After 30 minutes' contact at ambient temperature, 56 g of 3-nitrobenzaldehyde dissolved in tetrahydrofuran are poured in. After 1 hour, hydrolysis is carried out with 300 ml of water and then the solvent is concentrated. Following extraction with dichloromethane, washing the organic phase with water, drying over magnesium sulphate and concentration, the precipitate is taken up in diethyl ether and filtered off.

Workup

  1. additionare poured in
  2. waitAfter 1 hour
  3. customhydrolysis
  4. concentrationthe solvent is concentrated
  5. extractionextraction with dichloromethane
  6. washwashing the organic phase with water
  7. dry with materialdrying over magnesium sulphate and concentration
  8. filtrationfiltered off

Sources & evidence

ORD record
ord-83ff63ba8c864af485b35e9f901d6e97
Source dataset
uspto-grants-2004_08
Patent number
US06784183B2

Linked notes

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