Diethyl benzylphosphonate → Benzylphosphonic Acid

HRID 1870686Notes

Reaction equation

HRID 1870686 reaction equation
[CH2:1]([P:8](=[O:15])([O:12]CC)[O:9]CC)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>O>[CH2:1]([P:8](=[O:9])([OH:15])[OH:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 14122Diethyl benzylphosphonate

Product 1

HCID 81312Benzylphosphonic AcidYield 82%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Benzylphosphonic acid was prepared as follows. 200.40 g (878 mmoles) of diethyl benzylphosphonate was combined with 350 ml of distilled water and 350 ml of concentrated (~12 molar) hydrochloric acid. The resulting suspension was heated to reflux under nitrogen for 20 hours, whereupon a clear colorless solution was obtained. From this solution, 130 ml of aqueous distillate was removed. The residue was allowed to cool, forming a thick white slurry which was cooled in situ with an ice bath. The slurry was then filtered dry under vacuum, but not washed due to its fairly high solubility in water. The wet solid was then dried in a vacuum at 120° C. overnight. 123.37 g (82% yield) was obtained.

Workup

  1. concentrationof concentrated (~12 molar) hydrochloric acid
  2. temperatureThe resulting suspension was heated
  3. temperatureto reflux under nitrogen for 20 hours, whereupon a clear colorless solution
  4. customwas obtained
  5. customFrom this solution, 130 ml of aqueous distillate was removed
  6. temperatureto cool
  7. customforming a thick white slurry which
  8. temperaturewas cooled in situ with an ice bath
  9. filtrationThe slurry was then filtered
  10. customdry under vacuum
  11. washnot washed due to its fairly high solubility in water
  12. customThe wet solid was then dried in a vacuum at 120° C. overnight
  13. custom123.37 g (82% yield) was obtained

Sources & evidence

ORD record
ord-4c9da647027c46f4be9c284b8805b42c
Source dataset
uspto-grants-2000_08
Patent number
US06099895

Reaction notes

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