Diethyl 2-(trifluoromethyl)benzylphosphonate → Phosphonic acid, [[2-(trifluoromethyl)phenyl]methyl]-

HRID 1733819Notes

Reaction equation

HRID 1733819 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:17]=[CH:16][CH:15]=[CH:14][C:4]=1[CH2:5][P:6](=[O:13])([O:10]CC)[O:7]CC>Cl.CCO>[F:18][C:2]([F:1])([F:19])[C:3]1[CH:17]=[CH:16][CH:15]=[CH:14][C:4]=1[CH2:5][P:6](=[O:7])([OH:10])[OH:13]

Participants

4

Reactant 1

HCID 15818095Diethyl 2-(trifluoromethyl)benzylphosphonate

Product 1

HCID 15818096Phosphonic acid, [[2-(trifluoromethyl)phenyl]methyl]-Yield 46.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

The diethyl 2-trifluoromethylbenzylphosphonate (1.22 g, 4.12 mmol) was dissolved in a mixture of 50 mL of conc hydrochloric acid and 5 mL of EtOH and was heated at reflux temperature for 17 hours. After cooling the mixture in an ice bath, white crystalline acid was collected to give 0.46 g, 46% of the desired product, mp=190°-192° C.; D.C.I.M.S. [MH+, 241].

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 17 hours
  3. temperatureAfter cooling the mixture in an ice bath
  4. customwhite crystalline acid was collected

Sources & evidence

ORD record
ord-c435df6db3244c239e7e681be3701ccd
Source dataset
uspto-grants-1996_07
Patent number
US05532226

Reaction notes

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