Ethyl vinyl ether → Ethyl(2-ethoxyethyl)phosphinic acid

HRID 878922Notes

Reaction equation

HRID 878922 reaction equation
[CH2:1]([P:3]([OH:5])[OH:4])[CH3:2].[CH2:6]([O:8][CH:9]=[CH2:10])[CH3:7].[O-]S(OOS([O-])(=O)=O)(=O)=O.[Na+].[Na+]>O>[CH2:1]([P:3]([CH2:7][CH2:6][O:8][CH2:9][CH3:10])(=[O:5])[OH:4])[CH3:2]

Participants

5

Reactant 3

HCID 8023Ethyl vinyl etherHCID 62655Sodium PersulfateHCID 13411864Ethylphosphonous acid

Product 1

HCID 46235414Ethyl(2-ethoxyethyl)phosphinic acidYield 95.6%

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., 504 g (7 mol) of vinyl ethyl ether and 500 g of a 5% strength sodium peroxodisulfate solution (1.5 mol % based on vinyl ethyl ether) 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 953 g (82% of theory) of ethyl(2-ethoxyethyl)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-7281be16ebb2489c929bf77ac5a1b783
Source dataset
uspto-grants-2015_03
Patent number
US08987489B2

Reaction notes

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