Ethanol → Fenoprofen
Reaktionsgleichung
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]=1Komponenten
5
Versuchsvorschrift
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.