Abstract

ROMERO, Adriano L.; BAPTISTELLA, Lúcia H. B.; COELHO, Fernando  and  IMAMURA, Paulo M.. Resolution of ibuprofen: a project for an experimental organic chemistry course. Quím. Nova [online]. 2012, vol.35, n.8, pp. 1680-1685. ISSN 0100-4042.  http://dx.doi.org/10.1590/S0100-40422012000800031.

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)-(-)-α-methylbenzylamine with (±)-ibuprofen; separation and determination of absolute configuration of amides by ¹H NMR spectroscopy and GC analysis, and hydrolysis of amides to obtain (+)- and (-)-ibuprofen.

Keywords : resolution of ibuprofen; stereochemistry; NMR Spectroscopy.