A New Synthesis of 5-(1′,1′,1′-Trialkylmethyl) Resorcinols

Abstract

In connection with our investigation of synthetic cannabinoids as potential anticonvulsant drugs, we required various 5-(1′,1′,1′-trialkyl substituted) resorcinols as starting materials for the synthesis of cannabidiol analogs. The modification of the resorcinol side chain seems to enhance the biological activity of cannabinoids.¹ Several different methods have appeared in the literature for the synthesis of the simplest of such derivatives, 5-(1′,1′-dimethyl heptyl) 1 and 5-(1′,1′-dimethyl pentyl) resorcinols 2.^2,3,4,5 However, none of the published procedures are suitable for the introduction of alkyl groups other than methyl at C-1′. We therefore sought a more general, and shorter method which would permit the incorporation of a variety of alkyl groups and at the same time generate a quarternary carbon center at the 1′-position.