Synthesis and application of polymer-bound IBX toward the oxidation of phenols to o-quinones

CHED 458

Jason Phillips, jphillips20@mail.csuchico.edu, Chris Taylor, taychr@gmail.com, and Jinsong Zhang, jzhang2@csuchico.edu. Department of Chemistry and Biochemistry, California State University, Chico, 400 W. 1st St., Chico, CA 95929
In 2001 Rademann reported on the synthesis of a recyclable, polymer-supported o-iodoxybenzoic acid (IBX) reagent used for the efficient conversion of various aliphatic alcohols to their corresponding carbonyls. Later that year, Pettus discovered a successful regioselective method for the direct oxidation of phenols to ortho-quinones by IBX. We report a method that combines the usefulness of these two important aspects. A polymer-bound IBX reagent was synthesized and applied in the conversion of phenols to o-quinones. A significant advantage in using a polymer-supported IBX reagent for this process is related to the difficulty in isolating the extremely labile o-quinone. Negating the original need for the demanding work-up conditions required in separating the reactions products would hopefully result in higher yields of the desired o-quinone. Ultimately, the polymer-bound IBA reagent could be re-oxidized and used again.