p-Toluenesulfonic acid → Ethyl 2-chloro-3,5-difluoro-4-methylbenzoyl-acetate

HRID 34574Notes

Reaction equation

HRID 34574 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[Cl:12][C:13]1[C:31]([F:32])=[C:30]([CH3:33])[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>[Cl:12][C:13]1[C:31]([F:32])=[C:30]([CH3:33])[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 13657389Diethyl 2-chloro-3,5-difluoro-4-methylbenzoyl-malonate

Product 1

HCID 13657390Ethyl 2-chloro-3,5-difluoro-4-methylbenzoyl-acetateYield 63.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.1 g of p-toluenesulphonic acid is added to an emulsion of 65.1 g of crude diethyl 2-chloro-3,5-difluoro-4-methyl-benzoyl-malonate in 70 ml of water. The mixture is heated to the boiling point for 4.5 hours, with thorough stirring, the cooled emulsion is extracted several times with methylene chloride, the combined CH2Cl2 solutions are washed once with saturated NaCl solution and dried with Na2SO4 and the solvent is distilled off in vacuo. Fractionation of the residue under a fine vacuum gives 33 g of ethyl 2-chloro-3,5-difluoro-4-methylbenzoyl-acetate of boiling point 108°-118° C./0.09 mbar.

Workup

  1. temperatureThe mixture is heated to the boiling point for 4.5 hours, with thorough stirring
  2. extractionthe cooled emulsion is extracted several times with methylene chloride
  3. washthe combined CH2Cl2 solutions are washed once with saturated NaCl solution
  4. dry with materialdried with Na2SO4
  5. distillationthe solvent is distilled off in vacuo

Sources & evidence

ORD record
ord-0f67ad4cd38d4a54b3752986c0a4cebc
Source dataset
uspto-grants-1988_08
Patent number
US04762844

Reaction notes

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