Water → Ketoprofen

HRID 2108240Notes

Reaction equation

HRID 2108240 reaction equation
[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.O.[Mn]([O-])(=O)(=O)=[O:22].[K+]>C1C=CC=CC=1>[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:22])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 962WaterHCID 516875Potassium PermanganateHCID 14750257alpha-(3-(1-Phenylethenyl)phenyl)propionic acid

Product 1

HCID 3825Ketoprofen

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

α-(3-(1-Phenylethenyl)phenyl)propionic acid (35 g) obtained in Example 2 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 acidand 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. The aqueous layer 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.

Workup

  1. customto prepare a suspension
  2. stirringAfter the dropping, stirring
  3. customAfter the reaction, it
  4. additionby adding
  5. concentrationconcentrated sulfuric acidand
  6. additionwas treated
  7. additionby adding 35 g of sodium sulfite
  8. additionAfter that, 500 ml of water was added
  9. extractionextraction
  10. washThe ether solution was washed with water and it
  11. extractionwas extracted three times with 200 ml of 5% aqueous solution of sodium hydroxide
  12. additionby adding hydrochloric acid
  13. extractionextracted again three times with 150 ml of ether, which
  14. washby washing with water
  15. dry with materialdrying with anhydrous magnesium sulfate, and filtration
  16. customThe ether was then removed by reduced-pressure evaporation

Sources & evidence

ORD record
ord-24a3db2004f24267b0c1b50cf5a50f42
Source dataset
uspto-grants-1990_06
Patent number
US04937375

Reaction notes

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