Synthesis and PMR and mass spectra of potential metabolites and other derivatives of bis(2-ethylhexyl) phthalate.

The 3- and 4-hydroxylated derivatives of the plasticizer bis(2-ethylhexyl) phthalate and the monoesters derived from these hydroxylated derivatives were synthesized. The structures of the two 4-hydroxy monoesters were confirmed by lithium borohydride reduction to their corresponding hydroxymethylbenzoic acids, followed by cyclization of the reduced compounds to known phthalides. All compounds were characterized by PMR and mass spectra. The PMR data reiterate the difficulty in predicting chemical shifts in multisubstituted benzene rings.