Base Catalyzed Oxygenation of 3,5-Di-t-butylpyrocatechol and Its Related Compounds

Abstract
The oxygenation of 3,5-di-t-butylcatechol (1) and its related compounds 3,5-di-t-butyl-o-benzoquinone (2), 4,6-di-t-butylpyrogallol (3), 2,4-di-t-butyl-5-oxo-2-hexenedioic acid (4), 2,4-di-t-butyl-4-(carboxyhydroxymethyl)-2-buten-4-olide (5), and 3,5-di-t-butyl-6-carboxy-2-pyrone (6) in DMF–ButOK gave 2,4-di-t-butyl-4-hydroxy-2-buten-4-olide (7b). A possible mechanism and the relation between 4, 5, and 6, the products in aqueous alkaline autoxidation of 1 and 3, are discussed.