Hydrochloric Acid → Ethyl 3-trifluoromethylbenzylphosphonic acid

HRID 1463565Notes

Reaction equation

HRID 1463565 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][CH2:9][CH3:10].O.Cl>C(O)C.[OH-].[K+]>[CH2:9]([O:8][P:7]([CH2:6][C:5]1[CH:15]=[CH:16][CH:17]=[C:3]([C:2]([F:19])([F:1])[F:18])[CH:4]=1)(=[O:11])[OH:14])[CH3:10]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 11162251Diethyl 3-trifluoromethylbenzylphosphonate

Product 1

HCID 15819194Ethyl 3-trifluoromethylbenzylphosphonic acidYield 94.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14797Potassium HydroxideSolvent

Procedure

The diethyl 3-trifluoromethylbenzylphosphonate (10.0 g, 34.0 mmol) was dissolved in a mixture of 300 mL of 75% aqueous ethanol and 18.9 g of KOH and the resultant mixture was heated at reflux for 3 hours. The reaction mixture was poured into H2O, acidified with hydrochloric acid, and extracted with CHCl3 (3×500 mL). The chloroform extract was dried with anhydrous Na2SO4 and evaporated to yield 8.64 g (94.7%) of white solid product, mp=48°-51° C.; D.C.I.M.S.[MH+,269].

Workup

  1. temperatureat reflux for 3 hours
  2. extractionextracted with CHCl3 (3×500 mL)
  3. extractionThe chloroform extract
  4. dry with materialwas dried with anhydrous Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-6ab10440118b4a7b9aa72d933ba8d3b9
Source dataset
uspto-grants-1994_04
Patent number
US05300687

Reaction notes

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