By Adrian Coello

Faculty Mentor: Dr. Oldham

Abstract

Di(2-ethylhexyl)Phthalate (DEHP) is a chemical commonly used as plasticizer in polyvinyl chloride (PVC) to make it softer. DEHP is metabolized in the body to form primary and secondary metabolites; while DEHP is known to disrupt the endocrine system, there is little research on their toxicity The secondary metabolites of DEHP are not commercially available, so they must be synthesized to assess their toxicity. The first two approaches used to synthesize the secondary metabolites include the synthesis of metalloimines and enamines, which can be alkylated and hydrolyzed; however the metalloimines and enamines proved to be unstable. The third approach involved using the lithium diisopropylamide (LDA) pathway involving the alkylation of an ester followed by its reduction to an alcohol using lithium aluminum hydride (LAH), but the presence of byproducts in addition to difficulty handling these reagents made this approach difficult as well. The final and most promising method is the Corey epoxidation of a ketone followed by a Meinwald rearrangement and reduction to give a precursor to DEHP. Nuclear magnetic resonance (NMR) spectroscopy and gas chromatography – mass spectroscopy (GC-MS) were used to monitor the reaction at each step. 80% of the initial ketone was epoxidized and 100% of the Meinwald reaction product was reduced to the target alcohol. Further development will require the optimization of the Grignard synthesis of the starting ketone in the Corey epoxidation to be able to make each of the individual oxidative metabolites.