Vinyl Acetate → Ethyl(2-acetoxyethyl)phosphinic acid

HRID 2179552Notes

Reaction equation

HRID 2179552 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 1026 g (95% of theory) of ethyl(2-acetoxyethyl)phosphinic acid being obtained as 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-f9eac74ae3a849c5812f9f7e22207ef8
Source dataset
uspto-grants-2015_06
Patent number
US09068119B2

Reaction notes

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