Synthesis of naphthalenediols by aerobic oxidation of diisopropylnaphthalenes catalyzed by N-hydroxyphthalimide (NHPI)/α,α′-azobisisobutyronitrile (AIBN)

Naphthalenediols were successfully synthesized in a one-pot reaction through the oxidation of diisopropylnaphthalenes with air catalyzed by N-hydroxyphthalimide (NHPI) combined with azobisisobutyronitrile (AIBN) followed by decomposition with sulfuric acid. Thus, the oxidation of 2,6-diisopropylnaphthalene with air (20 atm) in the presence of AIBN (3 mol %) and NHPI (10 mol %) in CH3CN at 75degreesC for 21 h followed by treatment with 0.3 M H2SO4 gave 2,6-naphthalenediol in 92% yield.