Oxidative coupling of phenols using iodine in basic methanol

CHED 236

Michael W. Robinson, robins_mw@denison.edu and Thomas A. Evans, evans@denison.edu. Department of Chemistry and Biochemistry, Denison University, Ebaugh Laboratories, Granville, OH 43023
Phenol oxidation is an important anti-oxidant function in biological systems and oxidative coupling of phenols is observed in a variety of biosynthetic pathways. We have adapted to the teaching lab the oxidative coupling of 2,6-di-tert-butylphenol, which yields a diphenoquinone rapidly and in good yield. The reaction is performed using iodine as the oxidizing agent in basic methanol and is less hazardous than an alternative procedure that uses lead dioxide. Instructional opportunities created by our synthesis will be discussed.