Synthesis of 2-benzylcyclohexan-1-ol from cyclohexanone
Making a carbon-carbon bond at the alpha position of a carbonyl suggests using some kind of enolate chemistry. In contrast to an SN2 type reaction with an alkyl halide (which can give over-alkylation and competitive O-alkylation), an aldol condensation is a reliable way to construct the requisite C-C bond. Here cyclohexanone reacted with benzaldehyde under basic conditions gives an enone. Two subsequent reduction steps, hydrogenation followed by hydride addition to the ketone, give the target compound.