Catalytic hypervalent iodine oxidation of p-dialkoxybenzenes to p-quinones using 4-iodophenoxyacetic acid and Oxone

A catalytic hypervalent iodine oxidation of p-dialkoxybenzenes using 4-iodophenoxyacetic acid (1) and 2KHSO5 x KHSO4 x K2SO4 (Oxone) was developed. Reaction of p-dialkoxybenzenes (2) with a catalytic amount of 1 in the presence of Oxone as a co-oxidant in 2,2,2-trifluoroethanol-water (1 : 2) gave the corresponding p-quinones (3) in excellent yields without purification. This procedure was applied to synthesis of blattellaquinone (9), the sex pheromone of the German cockroach, Blattella germanica.