Water → 3-(Hydroxyphenylphosphinyl)propanoic acid

HRID 726832Notes

Reaction equation

HRID 726832 reaction equation
Cl[P:2](Cl)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:10]([O:18]OC(C)(C)C)(=[O:17])[C:11]1C=CC=C[CH:12]=1.C(O)(=[O:27])C=C.[OH2:29]>>[OH:29][P:2]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)([CH2:12][CH2:11][C:10]([OH:18])=[O:17])=[O:27]

Participants

5

Reactant 4

HCID 962WaterHCID 6581Acrylic AcidHCID 11966tert-Butyl peroxybenzoateHCID 12573Phenyl phosphorus dichloride

Product 1

HCID 112873403-(Hydroxyphenylphosphinyl)propanoic acid

Procedure

Using 501.2 g of dichlorophenylphosphine, 3.2 g of t-butyl peroxybenzoate, 201.8 g of acrylic acid, and 0.92 L of water, a rinse-purified 3-[hydroxy(phenyl)phosphinyl]propionic acid was prepared by the procedure described in U.S. Pat. No. 5,334,760, namely the steps of hydrolyzing the reaction mixture after completion of the reaction, cooling it, harvesting the resulting crystals by filtration, rinsing the crystal crop with water, and drying it. The yield was 564.9 g or 94.2%. From the area ratio of the respective signals on the 1H-NMR spectrum, the molar ratio of 3-[hydroxy(phenyl)phosphinyl]propionic acid to phenylphosphinic acid was found to be 99.10:0.9. The other components were traces below the detection limit.

Workup

  1. customafter completion of the reaction
  2. temperaturecooling it
  3. filtrationby filtration
  4. washrinsing the crystal crop with water
  5. customdrying it

Sources & evidence

ORD record
ord-672c6a8627e747fd89bac10dea930674
Source dataset
uspto-grants-1998_01
Patent number
US05710308

Reaction notes

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