Diethyl 4-(trifluoromethyl)benzylphosphonate → {[4-(Trifluoromethyl)phenyl]methyl}phosphonic acid

HRID 1733817Notes

Reaction equation

HRID 1733817 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:17]=[CH:16][C:6]([CH2:7][P:8](=[O:15])([O:12]CC)[O:9]CC)=[CH:5][CH:4]=1>Cl.CCO>[F:19][C:2]([F:1])([F:18])[C:3]1[CH:17]=[CH:16][C:6]([CH2:7][P:8](=[O:9])([OH:12])[OH:15])=[CH:5][CH:4]=1

Participants

4

Reactant 1

HCID 15819199Diethyl 4-(trifluoromethyl)benzylphosphonate

Product 1

HCID 15818094{[4-(Trifluoromethyl)phenyl]methyl}phosphonic acid

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

The diethyl 4-trifluoromethylbenzylphosphonate (3.0 g, 10 mmol) was dissolved in a mixture of 50 mL of conc hydrochloric acid and 5 mL of EtOH and heated at reflux for 17 hours. After cooling the mixture in an ice bath, white crystalline material was collected. Recrystallization of the solid from H2O gave 1.80 g, 75% of the analytically pure product: mp=163°-164° C.; D.C.I.M.S. [MH+, 241].

Workup

  1. temperatureheated
  2. temperatureat reflux for 17 hours
  3. temperatureAfter cooling the mixture in an ice bath
  4. customwhite crystalline material was collected
  5. customRecrystallization of the solid from H2O
  6. customgave 1.80 g, 75% of the analytically pure product

Sources & evidence

ORD record
ord-8bf5f816e2e44ab3a1e55542532e3647
Source dataset
uspto-grants-1996_07
Patent number
US05532226

Reaction notes

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