Tetraethyl (phenoxymethylene)-bisphosphonate → (Phenoxymethylene)-bisphosphonic acid

HRID 569606Notes

Reaction equation

HRID 569606 reaction equation
[O:1]([CH:8]([P:17](=[O:24])([O:21]CC)[O:18]CC)[P:9](=[O:16])([O:13]CC)[O:10]CC)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>Cl>[O:1]([CH:8]([P:17](=[O:18])([OH:21])[OH:24])[P:9](=[O:10])([OH:13])[OH:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 54483224Tetraethyl (phenoxymethylene)-bisphosphonate

Product 1

HCID 9816823(Phenoxymethylene)-bisphosphonic acid

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of tetraethyl (phenoxymethylene)-bisphosphonate (20 g) and 6N hydrochloric acid (150 ml) was refluxed overnight and the resulting solution was evaporated to dryness in vacuo. Residual hydrochloric acid was removed by repeated evaporation with absolute ethanol. The residue was taken up in acetone (7 ml) and ether (200 ml) was added. The crystalline product was filtered, washed with ether and dried in vacuo.

Workup

  1. temperaturewas refluxed overnight
  2. customthe resulting solution was evaporated to dryness in vacuo
  3. customResidual hydrochloric acid was removed
  4. customevaporation with absolute ethanol
  5. additionether (200 ml) was added
  6. filtrationThe crystalline product was filtered
  7. washwashed with ether
  8. customdried in vacuo

Sources & evidence

ORD record
ord-fed28e7d18344f6e97ba7c2d9727c9ab
Source dataset
uspto-grants-1988_03
Patent number
US04732998

Reaction notes

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