Cyclohexanol (CAS no.: ), which is also known as 1-Cyclohexanol, could be produced through the following synthetic routes.

A. . A 250-ml., two-necked, round-bottomed flask equipped with a magnetic stirring bar, an addition funnel for solids, and a reflux condenser bearing a nitrogen inlet is charged with 5.6 g. (0.21 mole) of aluminum powder and 16.2 g. (0.100 mole) of hexamethyldisiloxane and purged with nitrogen. The mixture is stirred and heated with an oil bath at 60° as 50.8 g. (0.200 mole) of iodine is added slowly through the addition funnel over 55 minutes. The bath temperature is raised to ca. 140°, and the mixture is heated under reflux for 1.5 hours. The reflux condenser is removed, and the flask is equipped for distillation at atmospheric pressure. The bath temperature is gradually raised from 140° to 210°, and the clear, colorless distillate is collected, yielding 32.6–35.3 g. (82–88%) of iodotrimethylsilane, b.p. 106–109°.

B. Cyclohexanol. A 25-ml., oven-dried, round-bottomed flask is charged with 1.722 g. (0.01524 mole) of cyclohexyl methyl ether. The flask is purged with nitrogen and sealed with a rubber septum. With oven-dried syringes, 4 ml. of chloroform, 0.5 g. (0.5 ml., 0.006 mole) of pyridine, and 4.8 g. (3.5 ml., 0.024 mole) of freshly prepared iodotrimethylsilane are injected into the flask in the order specified. When the iodotrimethylsilane is added, the solution becomes slightly yellow and a precipitate appears. The mixture is heated without stirring at 60° for 64 hours, after which the reaction is normally complete. Anhydrous methanol (2 ml.) is added, the mixture is cooled to room temperature, and the volatile components are removed on a rotary evaporator. Approximately 10 ml. of anhydrous diethyl ether is added, and the resulting suspension is filtered, removing pyridinium hydroiodide. The flask and the filter cake are washed thoroughly with ca. 50 ml. of anhydrous ether. The ether is evaporated, and the residual oil is purified by chromatography on 70 g. of silica gel packed with anhydrous ether in a 3 × 50 cm. glass column. The column is eluted with anhydrous ether, and 5–7 ml. fractions are collected and analyzed by TLC. Fractions containing product are combined and evaporated, affording 1.26–1.35 g. (83–89%) of cyclohexanol.