Sulfuric Acid → (4-Phenylcyclohexyl)methanol

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence