Synthesis of 2-substituted quinones, vitamin K3, and vitamin K1 from p-cresol. BF3·OEt2-cataIyzed methyl migration of 4-tert-butyldioxycyclohexadienones

摘要

BF3·OEt2-catalyzed methyl group migration of 4-methyl-4-terr-butyldioxycycIohexadienone, which is obtained by ruthenium-catalyzed oxidation of p-cresol with tert-butyl hydroperoxide, in hexafluoro-2-propanol/toluene gave toluquinone efficiently. The reaction can be applied to the regio-selective short-step syntheses of vitamin K3 and vitamin K1 from p-cresol.