Sulfuric Acid → Ketoprofen

HRID 620971

반응식

HRID 620971 반응식
[C:1]1([C:7]([C:9]2[CH:10]=[C:11]([CH:15]([CH3:19])[C:16]([OH:18])=[O:17])[CH:12]=[CH:13][CH:14]=2)=C)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Mn]([O-])(=O)(=O)=[O:21].[K+].S(=O)(=O)(O)O.S([O-])([O-])=O.[Na+].[Na+]>C1C=CC=CC=1.O>[C:7]([C:9]1[CH:10]=[C:11]([CH:15]([CH3:19])[C:16]([OH:18])=[O:17])[CH:12]=[CH:13][CH:14]=1)(=[O:21])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

7

반응물 4

HCID 1118Sulfuric AcidHCID 24437Sodium SulfiteHCID 516875Potassium PermanganateHCID 14750257alpha-(3-(1-Phenylethenyl)phenyl)propionic acid

생성물 1

HCID 3825Ketoprofen

시약·촉매·용매 2

HCID 241Benzene용매HCID 962Water용매2회

실험 절차

α-(3-(1-Phenylethenyl)phenyl)propionic acid (35 g) obtained in Example 5 was dissolved in 250 ml of benzene and 250 ml of water was further added thereto with vigorous stirring to prepare a suspension. Then, 2 liter of 2% aqueous solution of potassium permanganate was dropped little by little over 1.5 hours. After the dropping, stirring was continued for 18 hours at room temperature. After the reaction, it was acidified by adding concentrated sulfuric acid and was treated by adding 35 g of sodium sulfite. After that, 500 ml of water was added and extraction was carried out three times with 150 ml of ether. The ether solution was washed with water and it was extracted three times with 200 ml of 5% aqueous solution of sodium hydroxide. It was then acidified by adding hydrochloric acid and extracted again three times with 150 ml of ether, which was followed by washing with water, drying with anhydrous magnesium sulfate, and filtration. The ether was then removed by reduced-pressure evaporation. Finally, 20 g of α-(3-benzoylphenyl)propionic acid (ketoprofen) was obtained by re-crystallization from benzene/petroleum ether mixture. The melting point and spectrum were the same as those of an authentic sample.

후처리

  1. customto prepare a suspension
  2. stirringAfter the dropping, stirring
  3. customAfter the reaction, it
  4. additionwas treated
  5. extractionextraction
  6. washThe ether solution was washed with water and it
  7. extractionwas extracted three times with 200 ml of 5% aqueous solution of sodium hydroxide
  8. additionby adding hydrochloric acid
  9. extractionextracted again three times with 150 ml of ether, which
  10. washby washing with water
  11. dry with materialdrying with anhydrous magnesium sulfate, and filtration
  12. customThe ether was then removed by reduced-pressure evaporation

출처 및 근거

ORD 기록
ord-2d92beb792e744ee80ffd7f5de272afc
출처 데이터셋
uspto-grants-1989_04
특허 번호
US04822934

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