During Missouri Western's second semester of organic chemistry lab, experiments are selected that incorporate examples of key reactions and support the university's mission of applied learning.  The students commonly complete experiments like the formation and use of azo dyes, the preparation of a fluorescer and an oxalate ester for use in a chemiluminescence reaction, and the synthesis of lidocaine.  Many students find these relatable experiments memorable for years after graduation.  Recently a multi-step synthesis of ibuprofen, 2-(4-isobutylphenyl)propanoic acid, from 4-isobutylacetophenone was published in the Journal of Chemical Education by Kjonaas, Williams, Counce , and Crawley.  This procedure provides the students an occasion to complete a sodium borohydride reduction of a ketone, chlorination of an alcohol, and carboxylation of a Grignard reagent during the preparation of ibuprofen.  The student-prepared ibuprofen afforded them with the opportunity to learn about the United States Pharmacopeia and National Formulary (USP-NF).  While completing the synthesis, students examined the USP-NF monograph for ibuprofen and the general USP-NF test procedures.  Due to laboratory time limitations, the class completed only four of the nine USP-NF tests.  Completion of the Identification tests reinforced their knowledge of UV and IR spectroscopy.   Chromatography Purity, Limit of 4-Isobutylacetophenone, and Assay tests introduced them to HPLC for identification and quantification.

Synthesis and analysis of ibuprofen as an introduction to the United States Pharmacopeia and National Formulary (USP-NF) monographs

247th National Meeting (2014)

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