p-Toluenesulfonic acid → Ketoprofen

HRID 839863

Reaction equation

HRID 839863 reaction equation
[C:1]([CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C:10]1=O)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:16]([O:21]CC)(=[O:20])[C:17]([CH3:19])=O.C1(C)C=CC(S(O)(=O)=O)=CC=1>O>[C:1]([C:9]1[CH:14]=[C:13]([CH:12]=[CH:11][CH:10]=1)[CH:17]([CH3:19])[C:16]([OH:21])=[O:20])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 12041Ethyl pyruvateHCID 2756272-Benzoylcyclohexanone

Product 1

HCID 3825Ketoprofen

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 20 g of 2-benzoyl-cyclohexanone, 21.6 g of ethyl pyruvate and 0.2 g of p-toluenesulfonic acid is heated at 150° for 15 hours. There is removed that fraction which distills at 1 mm (Hg up to 150°) and the residue is heated for 10 hours at 230° with 5 parts by weight of pyridine hydrochloride. After cooling the raw reaction products are poured in water and extracted with ether. The residue which is obtained after evaporation of the solvent is steam distilled. The part which does not distil is extracted with ether, the ether solution is dried well over sodium sulfate and to the dried solution there is added diethylamine until a clearly alkaline pH is reached. There thus precipitates a mixture of diethylamine salts from which, through fractional crystallization with hexane-ethyl acetate there is obtained the diathylamine salt of m-benzoyl-hydratropic acid m.p. 102°-104°. The free acid is obtained therefrom with the usual techniques.

Workup

  1. temperatureis heated at 150° for 15 hours
  2. customThere is removed that fraction which
  3. distillationdistills at 1 mm (Hg up to 150°) and the residue
  4. temperatureis heated for 10 hours at 230° with 5 parts by weight of pyridine hydrochloride
  5. temperatureAfter cooling the raw
  6. customreaction products
  7. extractionextracted with ether
  8. customThe residue which is obtained
  9. customafter evaporation of the solvent
  10. distillationdistilled
  11. customThe part which does not distil
  12. extractionis extracted with ether
  13. dry with materialthe ether solution is dried well over sodium sulfate and to the dried solution there
  14. additionis added diethylamine until a clearly alkaline pH
  15. customThere thus precipitates
  16. additiona mixture of diethylamine salts from which
  17. customthrough fractional crystallization with hexane-ethyl acetate there

Sources & evidence

ORD record
ord-7736522a75c1430f81ba69aa1d6095c0
Source dataset
uspto-grants-1978_06
Patent number
US04097522

Linked notes

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