Potassium Hydroxide → Ketoprofen

HRID 1733637Notes

Reaction equation

HRID 1733637 reaction equation
CS[C:3]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15](OC)([O:22]C)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:10]=1)([CH3:8])[C:4]([O:6]C)=[O:5].[OH-].[K+]>[Zn].O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2].O>[C:15]([C:11]1[CH:10]=[C:9]([CH:3]([CH3:8])[C:4]([OH:6])=[O:5])[CH:14]=[CH:13][CH:12]=1)(=[O:22])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 2

HCID 14797Potassium HydroxideHCID 12819452Methyl alpha-methylthio-alpha-(m-(alpha,alpha-dimethoxybenzyl)phenyl)propionate

Product 1

HCID 3825KetoprofenYield 85.4%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 24463Copper sulfate pentahydrateCatalystHCID 962WaterSolvent2×

Procedure

Water (4 ml) was added to a mixture consisting of 269 mg of methyl α-methylthio-α-[m-(α,α-dimethoxybenzyl)phenyl]propionate, 500 mg of zinc powder and 80 mg of copper sulfate pentahydrate. Then, 500 mg of potassium hydroxide (85%) was added, and the mixture was stirred at the refluxing temperature for 44 hours. Water (4 ml) was further added, and with stirring, the mixture was heated under reflux for 3 hours. After cooling, the insoluble matter was separated by filtration, and washied with 20 ml of water. The filtrate and the washing were combined and adjusted to pH 1 with 2.0 ml of conc. hydrochloric acid. The mixture was stirred at 60° C. for 40 minutes and then, extracted three times with 20 ml of diethyl ether. The extract was washed with 10 ml of water, and dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was chromatographed on a silica gel column using methylene chloride as an eluent to afford 162 mg of α-(m-benzoylphenyl) propionic acid in a yield of 85%.

Workup

  1. stirringwith stirring
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 3 hours
  4. temperatureAfter cooling
  5. customthe insoluble matter was separated by filtration
  6. stirringThe mixture was stirred at 60° C. for 40 minutes
  7. extractionextracted three times with 20 ml of diethyl ether
  8. washThe extract was washed with 10 ml of water
  9. dry with materialdried over anhydrous sodium sulfate
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was chromatographed on a silica gel column

Sources & evidence

ORD record
ord-31b1378f5fc64490a71c977c9d9a6af4
Source dataset
uspto-grants-1980_12
Patent number
US04242519

Reaction notes

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