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

HRID 979147Notes

Reaction equation

HRID 979147 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-tetrafluorobenzoyl-malonate in 300 ml of water. The mixture is heated at the boiling point for 4.5 hours, with thorough stirring, the cooled emulsion is extracted several times with methylene chloride, the combined methylene chloride solutions are washed once with saturated sodium chloride solution and dried with sodium sulphate and the solvent is distilled off in vacuo. Fractionation of the residue under a fine vacuum gives 160.2 g of ethyl 2,3,4,5-tetrafluorobenzoylacetate of boiling point 75°-96° C./0.06-0.09 mbar.

Workup

  1. temperatureThe mixture is heated at the boiling point for 4.5 hours, with thorough stirring
  2. extractionthe cooled emulsion is extracted several times with methylene chloride
  3. washthe combined methylene chloride solutions are washed once with saturated sodium chloride solution
  4. dry with materialdried with sodium sulphate
  5. distillationthe solvent is distilled off in vacuo

Sources & evidence

ORD record
ord-b4676e98ecee43babcf9504a7d69cc98
Source dataset
uspto-grants-1987_05
Patent number
US04666920

Reaction notes

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