Efficient access to bisphenol A metabolites: Synthesis of monocatechol, mono-o-quinone, dicatechol, and di-o-quinone of bisphenol A

ABSTRACT

2-Iodoxybenzoic acid (IBX) oxidation of bisphenol A (BPA) is described. The selective production of either the mono-o-quinone or the di-o-quinone can be controlled by IBX stoichiometry. Isolated yields of quinone were greater than 80%. Previous synthesis of BPA-di-o-quinone using a large excess of Fremy’s salt produced only trace amounts of product. In addition to o-quinone products, both mono- and dicatechols of BPA can synthesize in high yield and isolated without chromatography. The more stable catechols can be quantitatively converted back to o-quinones using silver oxide oxidation in either acetone or DMF. These one-pot reactions provide access to four different BPA metabolites in high yield and significant scale.

GRAPHICAL ABSTRACT

KEYWORDS:

• Bisphenol A
• bisphenol A metabolites
• catechols
• genotoxic
• o-quinones

Additional information

Funding

This work was supported by the Fund for Undergraduate Research (FUSE) at the University of Nebraska at Omaha.