Isopropanol → 3-(Ethylbutoxyphosphinyl)propionic acid

HRID 2282077Notes

Reaction equation

HRID 2282077 reaction equation
[CH2:1]([P:3]([CH2:10][CH2:11][CH:12]=[O:13])(=[O:9])[O:4][CH2:5][CH2:6][CH2:7][CH3:8])[CH3:2].CC(C)=[O:16].OS(O)(=O)=O.O=[Cr](=O)=O.C(O)(C)C>CC(C)=O>[CH2:1]([P:3]([O:4][CH2:5][CH2:6][CH2:7][CH3:8])([CH2:10][CH2:11][C:12]([OH:16])=[O:13])=[O:9])[CH3:2]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 86656679Butyl ethyl(2-formylethyl)phosphinateHCID 131709961Jones' reagent

Product 1

HCID 866566803-(Ethylbutoxyphosphinyl)propionic acidYield 78%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

20.6 g (0.1 mop of butyl ethyl-(2-formylethyl)phosphinate (produced as in Example 10) in 500 ml of acetone are mixed 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 is additionally stirred for 3½ hours with ice cooling and 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 is 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 17.3 g (78% of theory) of 3-(ethylbutoxyphosphinyl)propionic acid as oil,

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
  5. customThe solvent of the filtrate was removed in vacuo
  6. customthe residue was recrystallized from acetone

Sources & evidence

ORD record
ord-c6844c7891094f8fbbfad8f0c80216b3
Source dataset
uspto-grants-2015_09
Patent number
US09139714B2

Reaction notes

Loading…