5,4'-DIMETHYL-2-METHOXYDIPHENYLETHER - A NEW PRODUCT FROM THE ANODIC-OXIDATION OF 4-METHYLANISOLE

Anodic oxidation of p-methylanisole (1a) in a solution of aqueous 0.05 M H2SO4/acetone cosolvent (1 : 1, v/v) on platinum gives 5,4'-dimethy l-2-methoxydiphenylether (3), a compound hitherto unexplored, in 50% y ield at a temperature below 15-degrees-C. Polymer products are formed in significant amounts (up to 60%) besides the diphenylether derivativ e (3) when the electrolytic oxidation proceeds in a solution containin g AcOH as cosolvent at room temperature. The reaction mechanism includ es both side chain anodic oxidation and ring 6e oxidation leading to a reactive intermediate, probably 3-methyl-5-methoxy-1,2-benzoquinone ( 5), whose polymeric products were also isolated.