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 dihydrona phthalenecarboxylates into substituted naphthalenes and tetrahydronaphthale nes was developed. Aromatization of substituted dihydronaphthalenecarboxyla tes with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone and subsequent treatment with eerie ammonium nitrate (CAN) gave the corresponding substituted napht halenecarboxylic acids. Alternatively, hydrogenolysis and subsequent treatm ent with CAN provided a way to tetrahydronaphthalenemethanols in good yield s.