Resolution of ibuprofen: a project for an experimental organic chemistry course

RESOLUTION OF IBUPROFEN: A PROJECT FOR AN EXPERIMENTAL ORGANIC CHEMISTRY COURSE. A practical and didactic sequence of experiments was proposed to illustrate the stereochemistry concept, optically active compounds, resolution of racemates, and use of the NMR technique, including 2D-COSY for identification of organic compounds, on a laboratory course for undergraduate students. The sequence was: extractions of racemic ibuprofen and chiral naproxen from commercial tablets; syntheses of diastereoisomeric amides reacting chiral (S)-(-)-alpha-methylbenzylamine with (+/-)-ibuprofen; separation and determination of absolute configuration of amides by H-1 NMR spectroscopy and GC analysis, and hydrolysis of amides to obtain (+)- and (-)-ibuprofen.