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

HRID 745478Notes

Reaction equation

HRID 745478 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[F:12][C:13]1[C:31]([F:32])=[C:30]([F:33])[C:29]([F:34])=[CH:28][C:14]=1[C:15]([CH:17](C(OCC)=O)[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[O:16]>O>[F:12][C:13]1[C:31]([F:32])=[C:30]([F:33])[C:29]([F:34])=[CH:28][C:14]=1[C:15]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[O:16]

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 71.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.3 g of p-toluenesulphonic acid is added to an emulsion of 284.8 g of crude diethyl 2,3,4,5-tetrafluorobenzoylmalonate in 300 ml of water. This mixture is heated to boiling, stirring vigorously for 5 hours, the cooled emulsion is extracted several times with methylene chloride, the combined methylene chloride solutions are washed once with saturated NaCl solution, dried with Na2SO4 and the solvent is removed by distillation in vacuo. Fractionation of the residue under high vacuum provides 160.2 g of ethyl 2,3,4,5-tetrafluorobenzoylacetate of boiling point 100°-110° C./0.09-0.1 mbar. Melting point 47°-49° C.

Workup

  1. temperatureThis mixture is heated
  2. extractionthe cooled emulsion is extracted several times with methylene chloride
  3. washthe combined methylene chloride solutions are washed once with saturated NaCl solution
  4. dry with materialdried with Na2SO4
  5. customthe solvent is removed by distillation in vacuo

Sources & evidence

ORD record
ord-7719340af36c4d3bb0c492e89dbae19a
Source dataset
uspto-grants-1986_07
Patent number
US04599334

Reaction notes

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