1-(1-Adamantyl)cyclohexanol (CAS no ), which is also known as Cyclohexanol, 1-tricyclo[3.3.1.13,7]dec-1-yl, could be produced from the below routes.

A. Active calcium. Freshly cut lithium (41.7 mg, 6.01 mmol) and biphenyl (1.020 g, 6.61 mmol) in freshly distilled tetrahydrofuran (THF, 15 mL) are vigorously stirred at room temperature under argon until the lithium is completely consumed (approx. 2 hr). The preformed lithium biphenylide is transferred via a cannula at room temperature to a well-dispersed suspension of calcium bromide (CaBr₂, 1.213 g, 6.07 mmol) in freshly distilled THF (15 mL). The reaction mixture is stirred for 1 hr at room temperature prior to use.

B. 1-(1-Adamantyl)cyclohexanol. Activated calcium prepared from preformed lithium biphenylide and excess CaBr2 in THF is cooled to -78°C. (543 mg, 2.52 mmol) in THF (10 mL) is added via a cannula at -78°C and the mixture is stirred at -78°C for 20 min. Excess cyclohexanone (520 mg, 5.30 mmol) is added via a disposable syringe at -78°C. The resulting mixture is gradually warmed to -20°C and stirred at -20°C for 30 min. The reaction mixture is then quenched with water at -20°C (20 mL) and warmed to room temperature. At this temperature it is filtered through a small pad of Celite which is washed with diethyl ether (Et₂O, 100 mL). The aqueous layer is extracted with Et₂O (3 × 50 mL). The combined organic phases are washed with water (15 mL) and dried over anhydrous magnesium sulfate (MgSO₄). Removal of the solvent and flash-column chromatography on silica gel (150 g, 230–400 mesh, eluted sequentially with hexane/EtOAc [0% to 15%]) affords reasonably pure 1-(1-adamantyl)cyclohexanol as a white solid. 1-(1-Adamantyl)cyclohexanol is recrystallized from hexanes as follows: The white crystals are dissolved in a limited amount of dichloromethane (CH₂Cl₂), hexane (15 mL) is added, the solvent is evaporated to 8 mL, more hexane (15 mL) is added, the solvent is evaporated to about 15 mL, and the solution is gradually cooled and allowed to stand for 24 hr to afford 469–476 mg (80–82% yield) of product as colorless needles, mp 169–171°C.