Isopropanol → [Hydroxy(ethyl)phosphinyl]acetic acid

HRID 1028263Notes

Reaction equation

HRID 1028263 reaction equation
[CH2:1]([P:3]([CH2:6][CH2:7][OH:8])(=[O:5])[OH:4])[CH3:2].CC(C)=[O:11].OS(O)(=O)=O.O=[Cr](=O)=O.C(O)(C)C>CC(C)=O>[CH2:1]([P:3]([OH:4])([CH2:6][C:7]([OH:11])=[O:8])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 46832563HCID 46832563, compoundHCID 131709961Jones' reagent

Product 1

HCID 15357685[Hydroxy(ethyl)phosphinyl]acetic acidYield 81%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

13.8 g (0.1 mol) of ethyl-(2-hydroxyethyl)phosphinic acid (produced as in Example 8) in 500 ml of acetone were admixed with 0.11 mol of Jones reagent (12.7 g of chromium trioxide in 36.7 ml of water and 11.0 ml of concentrated sulfuric acid) at 0° C. by dropwise addition. The reaction mixture was additionally stirred for 3½ hours with ice cooling and for 1 hour at room temperature. After 12 ml of isopropanol have been added, the mixture is poured onto ice-water. Volatile constituents are subsequently distilled off in vacuo. The residue was taken up in tetrahydrofuran and extracted. Insoluble salts were filtered off. The solvent of the filtrate was removed in vacuo and the residue was recrystallized from acetone to obtain 12.3 g (81% of theory) of 2-(ethylhydroxyphosphinyl)acetic acid as colorless solid.

Workup

  1. additionthe mixture is poured onto ice-water
  2. distillationVolatile constituents are subsequently distilled off in vacuo
  3. extractionextracted
  4. filtrationInsoluble salts were filtered off
  5. customThe solvent of the filtrate was removed in vacuo
  6. customthe residue was recrystallized from acetone

Sources & evidence

ORD record
ord-cbdc633ecbea4f15bd399a8c718cdee8
Source dataset
uspto-grants-2014_05
Patent number
US08735476B2

Reaction notes

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