Abstract
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′-dimethyl-2-methoxydiphenylether (3), a compound hitherto unexplored, in 50% yield at a temperature below 15°C. Polymer products are formed in significant amounts (up to 60%) besides the diphenylether derivative (3) when the electrolytic oxidation proceeds in a solution containing AcOH as cosolvent at room temperature. The reaction mechanism includes 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.
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Hlavatý, J. 5,4′-dimethyl-2-methoxydiphenylether: a new product from the anodic oxidation of 4-methylanisole. J Appl Electrochem 24, 989–992 (1994). https://doi.org/10.1007/BF00241189
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DOI: https://doi.org/10.1007/BF00241189