Hydrochloric Acid → ((3-Trifluoromethyl)phenyl)methyl-phosphonic acid

HRID 1733811Notes

Reaction equation

HRID 1733811 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:4]=[C:5]([CH:15]=[CH:16][CH:17]=1)[CH2:6][P:7](=[O:14])([O:11]CC)[O:8]CC.Cl>CCO>[F:18][C:2]([F:1])([F:19])[C:3]1[CH:4]=[C:5]([CH:15]=[CH:16][CH:17]=1)[CH2:6][P:7](=[O:8])([OH:11])[OH:14]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 11162251Diethyl 3-trifluoromethylbenzylphosphonate

Product 1

HCID 9881235((3-Trifluoromethyl)phenyl)methyl-phosphonic acidYield 85.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Diethyl 3-trifluoromethylbenzylphosphonate (3.0 g, 10.0 mmol) was dissolved in a mixture; of 50 mL of conc hydrochloric acid and 1.5 mL of EtOH and was heated at reflux for 17 hours. After cooling the clear reaction mixture in an ice-water mixture, the white crystalline solid which formed was collected to give 2.05 g (84.3%) of the analytical product, mp=163°-164° C. 300 MHz 1H NMR (DMSO-D6) δ, 7.40-7.75 (m, 4H, aromatic), 3.09 (d, 2H, J=21.5 Hz, PCH2). D.C.I.M.S.[MH+, 241].

Workup

  1. temperatureat reflux for 17 hours
  2. customthe white crystalline solid which formed
  3. customwas collected

Sources & evidence

ORD record
ord-b557fdc824884b9a8fe9abeb0754611e
Source dataset
uspto-grants-1996_07
Patent number
US05532226

Reaction notes

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