Allyl Alcohol → Ethyl-3-hydroxypropylphosphinic acid

HRID 2282071Notes

Reaction equation

HRID 2282071 reaction equation
[CH2:1]([P:3]([OH:5])[OH:4])[CH3:2].[CH2:6]([OH:9])[CH:7]=[CH2:8].[O-]S(OOS([O-])(=O)=O)(=O)=O.[Na+].[Na+]>O>[CH2:1]([P:3]([CH2:8][CH2:7][CH2:6][OH:9])(=[O:5])[OH:4])[CH3:2]

Participants

5

Reactant 3

HCID 7858Allyl AlcoholHCID 62655Sodium PersulfateHCID 13411864Ethylphosphonous acid

Product 1

HCID 86656674Ethyl-3-hydroxypropylphosphinic acidYield 89%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

564 g (6 mol) of ethylphosphonous acid (produced as in Example 1) 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. The reaction mixture is heated to 100° C. and 406 g (7 mol) of allyl alcohol and 500 g of a 5% sodium peroxodisulfate solution (1.5 mol % based on ally alcohol) is added dropwise at atmospheric pressure over 1 h. Then, the water is distilled off in vacuo, and the residue is taken up in THF and the insoluble salts are filtered off. The solvent of the filtrate is removed in vacuo to leave 812 g (89% of theory) of ethyl-3-hydroxypropylphosphinic acid as oil.

Workup

  1. additioninitially charged to a 5 l five-neck flask
  2. customequipped with thermometer
  3. temperaturereflux condenser, high-performance stirrer
  4. additionis added dropwise at atmospheric pressure over 1 h
  5. distillationThen, the water is distilled off in vacuo
  6. filtrationthe insoluble salts are filtered off
  7. customThe solvent of the filtrate is removed in vacuo

Sources & evidence

ORD record
ord-bc0a6eae70b040a7a0ac099d034d0067
Source dataset
uspto-grants-2015_09
Patent number
US09139714B2

Reaction notes

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