Synthesis of 1,2-disubstituted naphthalenes and tetrahydronaphthalenes from dihydronaphthalenes obtained by conjugate addition of organolithium reagents to 2,6-bis(tert-butyl)-4-methoxyphenyl naphthalenecarboxylates

A method of the conversion of 2,6-bis(tert-butyl)-4-methoxyphenyl dihydronaphthalenecarboxylates into substituted naphthalenes and tetrahydronaphthalenes was developed. Aromatization of substituted dihydronaphthalenecarboxylates with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone and subsequent treatment with ceric ammonium nitrate (CAN) gave the corresponding substituted naphthalenecarboxylic acids. Alternatively, hydrogenolysis and subsequent treatment with CAN provided a way to tetrahydronaphthalenemethanols in good yields.