p-Toluenesulfonic acid → Ethyl 3-oxo-(2,3,4,5-tetrafluorophenyl)propanoate

HRID 845024Notes

Reaction equation

HRID 845024 reaction equation
[F:1][C:2]1[C:20]([F:21])=[C:19]([F:22])[C:18]([F:23])=[CH:17][C:3]=1[C:4]([CH:6](C(OCC)=O)[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5].C1(C)C=CC(S(O)(=O)=O)=CC=1>O>[F:1][C:2]1[C:20]([F:21])=[C:19]([F:22])[C:18]([F:23])=[CH:17][C:3]=1[C:4]([CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 135649731,3-Diethyl 2-(2,3,4,5-tetrafluorobenzoyl)propanedioate

Product 1

HCID 600916Ethyl 3-oxo-(2,3,4,5-tetrafluorophenyl)propanoateYield 35.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Diethyl 2,3,4,5-tetrafluorobenzoylmalonate (2.9 g) and p-toluenesulfonic acid (15 mg) are added to water (5 ml), and the mixture is refluxed for 3 hours. After cooling, the reaction mixture is extracted with dichloromethane. The dichloromethane layer is washed with saturated aqueous sodium chloride solution and dried over magnesium sulfate. After distilling off the solvent under reduced pressure, the residue is purified by silica gel column chromatography (solvent, chloroform: n-hexane=1:1) to give ethyl α-(2,3,4,5-tetrafluorobenzoyl)acetate (0.8 g), m.p. 44.5°-45.5° C.

Workup

  1. temperaturethe mixture is refluxed for 3 hours
  2. temperatureAfter cooling
  3. extractionthe reaction mixture is extracted with dichloromethane
  4. washThe dichloromethane layer is washed with saturated aqueous sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. distillationAfter distilling off the solvent under reduced pressure
  7. customthe residue is purified by silica gel column chromatography (solvent, chloroform: n-hexane=1:1)

Sources & evidence

ORD record
ord-c4b6fbd8d96e443b8051e100ce23d84b
Source dataset
uspto-grants-1988_07
Patent number
US04755513

Reaction notes

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