Vinyl Acetate → Ethyl(2-acetoxyethyl)phosphinic acid

HRID 1028261Notes

Reaction equation

HRID 1028261 reaction equation
[CH2:1]([P:3]([OH:5])[OH:4])[CH3:2].[C:6]([O:9][CH:10]=[CH2:11])(=[O:8])[CH3:7].[O-]S(OOS([O-])(=O)=O)(=O)=O.[Na+].[Na+]>O>[CH2:1]([P:3]([CH2:11][CH2:10][O:9][C:6](=[O:8])[CH3:7])(=[O:5])[OH:4])[CH3:2]

Participants

5

Reactant 3

HCID 7904Vinyl AcetateHCID 62655Sodium PersulfateHCID 13411864Ethylphosphonous acid

Product 1

HCID 46235412Ethyl(2-acetoxyethyl)phosphinic acidYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

564 g (6 mol) of ethylphosphonous acid are dissolved in 860 g of water and initially charged to a 5 l five-neck flask equipped with thermometer, reflux condenser, high-performance stirrer and dropping funnel. After heating the reaction mixture to 100° C., 602 g (7 mol) of vinyl acetate and 500 g of a 5% strength sodium peroxodisulfate solution (1.5 mol % based on vinyl acetate) are added dropwise at atmospheric pressure over 1 h. The water is then distilled off in vacuo. The residue is taken up in tetrahydrofuran and the insoluble salts are filtered off. The solvent of the filtrate is removed in vacuo. Chromatographic purification leaves 1.026 g (95% of theory) of ethyl-(2-acetoxyethyl)phosphinic acid being obtained as an oil.

Workup

  1. additioninitially charged to a 5 l five-neck flask
  2. customequipped with thermometer
  3. temperaturereflux condenser, high-performance stirrer
  4. distillationThe water is then distilled off in vacuo
  5. filtrationthe insoluble salts are filtered off
  6. customThe solvent of the filtrate is removed in vacuo
  7. customChromatographic purification

Sources & evidence

ORD record
ord-a00a39ae7eb34a309dc8c78877c0df8b
Source dataset
uspto-grants-2014_05
Patent number
US08735476B2

Reaction notes

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