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

HRID 1463570Notes

Reaction equation

HRID 1463570 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-ea7351dfea5444b891650cde59aff8a0
Source dataset
uspto-grants-1994_04
Patent number
US05300687

Reaction notes

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