Acetic Acid → 2-Cyanoethyl(n-butyl)phosphinic acid ethyl ester

HRID 1077697Notes

Reaction equation

HRID 1077697 reaction equation
[CH2:1]([O:3][PH:4]([CH2:6][CH2:7][CH2:8][CH3:9])=[O:5])[CH3:2].[C:10](#[N:13])[CH:11]=[CH2:12].[Na].C(O)(=O)C>C(O)C>[CH2:1]([O:3][P:4]([CH2:12][CH2:11][C:10]#[N:13])([CH2:6][CH2:7][CH2:8][CH3:9])=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7855AcrylonitrileHCID 5360545SodiumHCID 178454912HCID 178454912, compound

Product 1

HCID 104428632-Cyanoethyl(n-butyl)phosphinic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

15.0 g of n-butylphosphinic acid ethyl ester and 5.3 g of acrylonitrile are dissolved under argon in 25 ml of ethanol. The solution is cooled to 10°, and a solution of 1.15 g of sodium in 50 ml of ethanol is added dropwise, whereupon the exothermic reaction takes place. The mixture is then heated under reflux for one hour and cooled to room temperature, and 3.3 g of glacial acetic acid are added. The solvent is removed and the residue is taken up in dichloromethane. The resulting solution is washed with water, dried over sodium sulfate and concentrated by evaporation. The oil that remains is distilled, yielding 2-cyanoethyl(n-butyl)phosphinic acid ethyl ester having a boiling point of 120° (10-1 bar).

Workup

  1. temperatureThe solution is cooled to 10°
  2. temperatureThe mixture is then heated
  3. temperatureunder reflux for one hour
  4. customThe solvent is removed
  5. washThe resulting solution is washed with water
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated by evaporation
  8. distillationThe oil that remains is distilled

Sources & evidence

ORD record
ord-8e096b22c7d145c889b17fda4daa6c6b
Source dataset
uspto-grants-1996_08
Patent number
US05545631

Reaction notes

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