1-Butanol → 3-(Hydroxymethylphosphinyl)propionic acid

HRID 23971Notes

Reaction equation

HRID 23971 reaction equation
[OH2:1].[CH3:2][P:3]([OH:5])[OH:4].[CH2:6]([OH:10])[CH2:7][CH2:8]C>>[C:6]([CH2:7][CH2:8][P:3]([CH3:2])(=[O:5])[OH:4])([OH:10])=[O:1]

Participants

4

Reactant 3

HCID 2631-ButanolHCID 962WaterHCID 77879Methylphosphonous acid

Product 1

HCID 847883-(Hydroxymethylphosphinyl)propionic acid

Procedure

Hydrolysis of Dibutyl Carboxyethylmethylphosphinate 528 g (2 mol) of the dibutyl carboxyethylmethylphosphinate obtained according to Example 4 are charged to a 1 l five-neck flask fitted with thermometer, reflux condenser, high-speed stirrer and dropping funnel. At 160° C., 500 ml of water are metered in over 4 h and a butanol-water mixture is distilled off. 281 g of butanol are obtained, which corresponds to 95% of theory. The distillatively removed butanol is re-used to esterify the methylphosphonous acid. 300 g of carboxyethylmethylphosphinic acid are obtained as a white solid having a melting point of about 95° C. and a 31P NMR purity of >97%.

Workup

  1. customobtained
  2. additionare charged to a 1 l five-neck flask
  3. customfitted with thermometer
  4. temperaturereflux condenser, high-speed stirrer
  5. customAt 160° C.
  6. customare metered in over 4 h
  7. distillationa butanol-water mixture is distilled off
  8. custom281 g of butanol are obtained

Sources & evidence

ORD record
ord-8422a13963d249619fce4f39924e8fa1
Source dataset
uspto-grants-2005_02
Patent number
US06855757B2

Reaction notes

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