Ethanol → Fenoprofen

HRID 1759431Notes

Reaction equation

HRID 1759431 reaction equation
C(O)C.[O:4]([C:11]1[CH:12]=[C:13]([CH:17]([CH3:20])[C:18]#N)[CH:14]=[CH:15][CH:16]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[OH-:21].[K+].[OH2:23]>>[O:4]([C:11]1[CH:12]=[C:13]([CH:17]([CH3:20])[C:18]([OH:23])=[O:21])[CH:14]=[CH:15][CH:16]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 962Water2×HCID 14797Potassium HydroxideHCID 1180062-(3-Phenoxyphenyl)propanenitrile

Product 1

HCID 3342FenoprofenYield 90%

Procedure

Ethanol (5 ml) and 1 ml of water were added to 191 mg of alpha-(m-phenoxyphenyl)propionitrile, and 490 mg of potassium hydroxide was added. The mixture was heated under reflux for 5 hours. The reaction mixture was cooled, and 10 ml of water was added. The mixture was washed with 10 ml of ether three times. Conc. hydrochloric acid was added to the aqueous layer to adjust its pH to below 1, and then it was extracted with 10 ml of ether three times. The extract was washed with 20 ml of water two times, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel; methylene chloride and ether) to afford 187 mg (yield 90%) of alpha-(m-phenoxyphenyl)-propionic acid as a colorless oil. The IR spectrum of this product coincided completely with that of an authentic sample.

Workup

  1. additionwas added
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 5 hours
  4. temperatureThe reaction mixture was cooled
  5. washThe mixture was washed with 10 ml of ether three times
  6. additionConc. hydrochloric acid was added to the aqueous layer
  7. extractionit was extracted with 10 ml of ether three times
  8. washThe extract was washed with 20 ml of water two times
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was purified by column chromatography (silica gel; methylene chloride and ether)

Sources & evidence

ORD record
ord-dec99540db2e4a278b8618e285243c11
Source dataset
uspto-grants-1982_07
Patent number
US04340740

Reaction notes

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