1-Phenylcyclohexanol → 1-Phenylcyclohexene

Participants

Reaction Steps

4-Propylcyclohexanone is dissolved in a solvent, e.g., dichloromethane, and heated with heavy water (D2O) in the presence of a base to obtain 4-propylcyclohexanone-2,2,6,6-d4, which is then reacted with a Grignard reagent prepared from 1-ethoxy-4-bromobenzene. The resulting d4 -phenylcyclohexanol derivative is dehydrated to obtain a d3 -phenylcyclohexene derivative. The d3 -phenylcyclohexene derivative is catalytically reduced, and the cis-compound is removed to obtain 1-(trans-4-propylcyclohexyl-2,2,6-d3)-4-ethoxybenzene. ##STR60##

Provenance & Evidence