Acetic Acid → HCID 19090879, compound

HRID 729142Notes

Reaction equation

HRID 729142 reaction equation
[O-]CC.[Na+].[C:5](#[N:8])[CH:6]=[CH2:7].[CH2:9]([O:12][P:13]([CH:15]([O:20][CH2:21][CH2:22][CH3:23])[O:16][CH2:17][CH2:18][CH3:19])[OH:14])[CH2:10]C.C(O)(=O)C>C(O)C>[C:5]([CH2:6][CH2:7][P:13]([CH:15]([O:16][CH2:17][CH2:18][CH3:19])[O:20][CH2:21][CH2:22][CH3:23])(=[O:14])[O:12][CH2:9][CH3:10])#[N:8]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7855AcrylonitrileHCID 2723922Sodium ethoxideHCID 53942597HCID 53942597, compound

Product 1

HCID 19090879HCID 19090879, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of sodium ethoxide in absolute ethanol (0.48 g of sodium metal in 15 ml of absolute ethanol) is cooled to 0° under nitrogen or argon. A solution of 2.72 g of acrylonitrile and 12.2 g of di-n-propyloxymethylphosphonous acid n-propylester in 50 ml of absolute ethanol is added at such a rate that the temperature does not exceed 5°. After the addition is completed, the solution is allowed to warm to room temperature and stirred overnight. After addition of 1.22 g of glacial acetic acid, the reaction mixture is concentrated in vacuo. Theresidue is partitioned between ethyl acetate and water and the organic phase separated. After drying over anhydrous magnesium sulphate the solvent is evaporated in vacuo to afford an oil. Chromatography on silica-gel yields ethyl 2-cyanoethyl(di-n-propyloxymethyl)phosphinate as acolourless oil.

Workup

  1. customdoes not exceed 5°
  2. additionAfter the addition
  3. concentrationthe reaction mixture is concentrated in vacuo
  4. customTheresidue is partitioned between ethyl acetate and water
  5. customthe organic phase separated
  6. dry with materialAfter drying over anhydrous magnesium sulphate the solvent
  7. customis evaporated in vacuo
  8. customto afford an oil

Sources & evidence

ORD record
ord-b5804bc4385842f9ba0676cd4918a57f
Source dataset
uspto-grants-1991_09
Patent number
US05051524

Reaction notes

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