Sulfuric Acid → (4-Phenylcyclohexyl)methanol

Participants

Reaction Conditions

Reaction Steps

Dried tetrahydrofuran (THF) (420 ml) was added to aluminum-lithium hydride (11.1 g, 0.293 mol) and the mixture was vigorously agitated. To the mixture was dropwise added a solution of methyl trans-4-phenylcyclohexanecarboxylate (II) (64.0 g, 0.293 mol) dissolved in THF (70 ml) while the reaction temperature was kept at 20° C. or lower. After completion of the dropwise addition, the mixture was warmed up to 55° C., reacted for 2 hours and cooled. Ethyl acetate (12 ml) and water (100 ml) were then added, followed by adding 18% sulfuric acid (350 ml) to give two separated layers: tetrahydrofuran layer and water layer. n-Heptane (200 ml) was added and the mixture was transferred into a separating funnel, followed by washing it with water (500 ml), washing with a 2% sodium carbonate aqueous solution (500 ml) and further washing with water till the aqueous layer becomes neutral. Heptane and THF were distilled off and the solid remaining in the distilation kessel was recrystallized from heptane (20 ml), and separated by filtration, followed by drying crystals to obtain 4-phenyl-cyclohexylmethylalcohol (III) (51.4 g) having a melting point of 47.3°~48.5° C.

Provenance & Evidence