Methanol → Ketoprofen

HRID 1759444Notes

Reaction equation

HRID 1759444 reaction equation
CO.[C:3]([C:11]1[CH:12]=[C:13]([CH:17]([CH3:20])[C:18]#N)[CH:14]=[CH:15][CH:16]=1)(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[OH-:21].[Na+].[OH2:23]>>[C:3]([C:11]1[CH:12]=[C:13]([CH:17]([CH3:20])[C:18]([OH:23])=[O:21])[CH:14]=[CH:15][CH:16]=1)(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 962Water2×HCID 14798Sodium HydroxideHCID 393252-(3-Benzoylphenyl)propanenitrile

Product 1

HCID 3825KetoprofenYield 84%

Procedure

Methanol (1 ml) and 1 ml of water were added to 200 mg of alpha-(m-benzoylphenyl)propionitrile, and 50 mg of sodium hydroxide was added. The mixture was heated under reflux for 24 hours. The reaction mixture was cooled, and after adding 10 ml of water, extracted with 5 ml of ether three times. The extract was washed with 5 ml of water three times. The aqueous layers were combined, and after adding conc. hydrochloric acid to adjust the pH to below 1, were extracted with 5 ml of ether three times. The extract was washed with 5 ml of water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The oily residue was purified by column chromatography (silica gel; methylene chloride and ethyl acetate) to afford 181 mg (yield 84%) of alpha-(m-benzoylphenyl)propionic acid as colorless crystals. The IR spectrum and NMR spectrum of the product coincided completely with those of an authentic sample.

Workup

  1. additionwas added
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 24 hours
  4. temperatureThe reaction mixture was cooled
  5. extractionextracted with 5 ml of ether three times
  6. washThe extract was washed with 5 ml of water three times
  7. additionafter adding conc. hydrochloric acid
  8. extractionwere extracted with 5 ml of ether three times
  9. washThe extract was washed with 5 ml of water
  10. dry with materialdried over anhydrous magnesium sulfate
  11. concentrationconcentrated under reduced pressure
  12. customThe oily residue was purified by column chromatography (silica gel; methylene chloride and ethyl acetate)

Sources & evidence

ORD record
ord-d821629246504ba1887614c02d53878e
Source dataset
uspto-grants-1982_07
Patent number
US04340740

Reaction notes

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