Sulfuric Acid → 3-[Ethyl(hydroxy)phosphoryl]propanoic acid

HRID 1028258Notes

Reaction equation

HRID 1028258 reaction equation
[Na+].[CH2:2]([P:4]([OH:11])([CH2:6][CH2:7][C:8]([O-:10])=[O:9])=[O:5])[CH3:3].S(=O)(=O)(O)O>O>[CH2:2]([P:4]([OH:11])([CH2:6][CH2:7][C:8]([OH:10])=[O:9])=[O:5])[CH3:3]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 1317314203-(Ethylhydroxyphosphinyl)propionic acid sodium salt

Product 1

HCID 190110643-[Ethyl(hydroxy)phosphoryl]propanoic acidYield 98%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

630 g (3 mol) of 3-(ethylhydroxyphosphinyl)propionic acid sodium salt (produced as in Example 16) are dissolved in 860 g of water and initially charged into a 5 l five-neck flask equipped with thermometer, reflux condenser, high-performance stirrer and dropping funnel and neutralized by addition of about 147 g (1.5 mol) of concentrated sulfuric acid. The water is subsequently distilled off in vacuo. The residue is taken up in ethanol and the insoluble salts are filtered off. The solvent of the filtrate is removed in vacuo to leave 488 g (98% of theory) of 3-(ethylhydroxy-phosphinyl)propionic acid as a solid material.

Workup

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

Sources & evidence

ORD record
ord-e8275dfa450d4b34a6186bb1fe055b14
Source dataset
uspto-grants-2014_05
Patent number
US08735477B2

Reaction notes

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