p-Toluenesulfonic acid → Ketoprofen

HRID 839863

反応式

HRID 839863 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 3825Ketoprofen

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-7736522a75c1430f81ba69aa1d6095c0
出典データセット
uspto-grants-1978_06
特許番号
US04097522

関連ノート

読み込み中…