3-Phenyl-1-propanol and 3-phenyl-1-butanol can be obtained with relative ease by a two-step synthesis from styene or α-methylstyrene. In the first step a Prins’ reaction with formaldehyde affords the respective substituted 1,3-dioxane (Reaction 1) which, in the second step, undergoes hydrogenolysis to yield a phenyl substituted alcohol (Reaction 11).
Similarly, 3-phenyl-1-butanol may be obtained from α-methylstyrene via 4-methyl-4-phenyl-1,3-dioxane. Both phenyl substituted alcohols are important fragrant compounds themselves, similar to a number of their derivatives.
This study reports an investigation of the hydrogenation of aromatic rings of these alcohols, leading to the respective 3-cyclohexyl-1-alkanols (Reactions III and IV).