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

HRID 2282078Notes

Reaction equation

HRID 2282078 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>>[CH2:2]([P:4]([OH:11])([CH2:6][CH2:7][C:8]([OH:10])=[O:9])=[O:5])[CH3:3]

Participants

3

Reactant 2

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

Product 1

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

Procedure

In the aqueous solution of 420 g (2 mol) of 3-(ethylhydroxyphosphinyl)propionic acid sodium salt (produced as in Example 12) is rendered acidic with about 196 g of concentrated sulfuric acid and the water is distilled off in vacuo. The residue was taken up in tetrahydrofuran and extracted. The insoluble salts were filtered off. The solvent of the filtrate was removed in vacuo and the residue was recrystallized from acetone to obtain 325 g (98% of theory) of 3-(ethylhydroxyphosphinyl)-propionic acid as colorless solid.

Workup

  1. distillationthe water is distilled off in vacuo
  2. extractionextracted
  3. filtrationThe insoluble salts were filtered off
  4. customThe solvent of the filtrate was removed in vacuo
  5. customthe residue was recrystallized from acetone

Sources & evidence

ORD record
ord-1e84d5a3e98a470ca21dece40bd98be2
Source dataset
uspto-grants-2015_09
Patent number
US09139714B2

Reaction notes

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