Sulfuric Acid → (4-Phenylcyclohexyl)methanol

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Dry tetrahydrofuran (THF) (420 ml) was added to lithiumaluminum hydride (11.1 g, 0.293 mol) and the mixture was vigorously agitated, followed by dropwise adding to the mixture, a solution obtained by dissolving trans-4-phenylcyclohexanecarboxylic acid methyl ester (II) (64.0 g, 0.293 mol) in THF (70 ml), while keeping the reaction temperature at 20° C. or lower. After completion of the dropwise addition, the reaction mixture was warmed up to 55° C., reacted for 2 hours and cooled, followed by adding ethyl acetate (12 ml) and water (100 ml), and then adding 18% sulfuric acid (350 ml) to form two separated layers of a tetrahydrofuran layer and an aqueous layer. n-Heptane (200 ml) was added to the former layer and the mixture was transferred into a separating funnel, followed by washing with water (500 ml), washing with 2% aqueous solution of sodium carbonate (500 ml), further washing with water till the aqueous layer became neutral, distilling off n-heptane and THF, recrystallizing solid as still residue from n-heptane (20 ml), filtering off the resulting crystals and drying to obtain 4-phenylcyclohexylmethanol (III) (51.4 g). M.P. 47.3°~48.5° C.

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