1-Trifluoromethyl-1-cyclohexanol (CAS no.: ), which is also known as Cyclohexanol, 1-(trifluoromethyl)-, could be produced from the below routes.

A. (Trifluoromethyl)trimethylsilane (CAS no ). A 2-L, three-necked flask is fitted with an efficient, overhead, sealed mechanical stirrer, a cold-finger condenser (30-cm in length and 8-cm in diameter) and a rubber septum. The top outlet of the condenser is attached to an oil bubbler. The flask is flushed with dry nitrogen and charged with 118.8 g (1.09 mol) of chlorotrimethylsilane in 100 mL of anhydrous benzonitrile. The septum is replaced quickly under dry nitrogen with a 500-mL Ace dry ice gas condenser trap (15-cm in length and 8-cm in diameter). The outlet of the trap is protected from moisture by a tube packed with potassium hydroxide and the inlet is connected by tygon tubing to a cylinder of bromotrifluoromethane. The 2-L flask is immersed in a dry ice-acetone bath maintained at -30°C and the condensers are filled with dry ice-acetone mixture (-78°C). The cylinder is opened and 250 mL (d = 1.94 g/mL,2 485 g, 3.25 mol) of bromotrifluoromethane is condensed into the 500-mL Ace reservoir. Stirring is started, and the condensed liquid bromotrifluoromethane is gradually added to the vessel at -30°C by slowly warming the reservoir to -45°C to -50°C. The resulting white slurry is further cooled to -60°C. The Ace dry ice gas condenser trap is disconnected under dry nitrogen and replaced with a 600-mL, pressure-equalizing dropping funnel containing a solution of 325.0 g (1.31 mol) of hexaethylphosphorous triamide in 250 mL of dry benzonitrile. This solution is added with stirring at -60°C to the white slurry mixture over a period of 2.5 hr. After the addition is complete, the reaction mixture is stirred for an additional hour at -60°C, and then allowed to warm gradually to room temperature (25°C) over a period of 14 hr, during which time it turns clear yellow. The condenser and dropping funnel are removed and replaced by a glass stopper and joint adapter with its glass tube connected to two, 250-mL, dry ice/acetone-cooled traps; then aspirator vacuum (ca. 20 mm) is applied. The reaction flask is gently warmed to 50°C during which time (3 hr) all the volatile material collects in the cooled traps. The cooling baths are removed and the material in the traps is brought to 0°C. The colorless liquid is transferred quickly to a 250-mL separatory funnel, washed rapidly with ice cold water (3 × 100 mL), and the top organic product layer is separated. The product is dried over 5 g of anhydrous magnesium sulfate, and the dry liquid is decanted into a 250-mL flask. The product is fractionally distilled through a 15-cm column packed with glass helices. Three fractions are collected. The first minor fraction (bp 45–54°C) and the second major fraction (bp 54–55°C) contain the main quantity of (trifluoromethyl)trimethylsilane. The third minor fraction (bp 55–65°C) consists mainly of hexamethyldisiloxane with a small quantity of product (trifluoromethyl)trimethylsilane . The first and second fractions are combined to yield 116.9 g (75%) of clear liquid product, bp 54–55°C.

B. 1-Trifluoromethyl-1-cyclohexanol (CAS no ). A 250-mL, three-necked, round-bottomed flask equipped with a magnetic stirring bar, rubber septum, and a reflux condenser is attached to a nitrogen source to maintain a positive pressure and the other neck is closed with a glass stopper. (70 mL) and 19.2 g (0.13 mol) of (trifluoromethyl)trimethylsilane are introduced into the flask through the septum using dry syringes. The flask is immersed in an ice-water bath (0°C), and a solution of 10.2 g (0.104 mol) of cyclohexanone in 50 mL of tetrahydrofuran is added to the stirred solution of (trifluoromethyl)trimethylsilane using a syringe. trihydrate (33 mg) catalyst is transferred into the reaction vessel. As the exothermic reaction proceeds, a yellowish brown color develops with the initial evolution of fluorotrimethylsilane. The reaction mixture is stirred at 0°C for 30 min and then the cooling bath is removed. The reaction mixture is brought to room temperature and stirred for an additional hour. The reaction mixture is periodically analyzed by GC-MS and the reaction is complete within 1 hr at 25°C. To the reaction mixture that contains crude 1-trifluoromethyl-1-O-(trimethylsilyl)cyclohexane are added 25 mL of tetrahydrofuran and 40 mL of 3 N hydrochloric acid. The mixture is stirred at room temperature for 8 hr and then transferred to a 500-mL separatory funnel containing 50 mL of water. The product is extracted with 50 mL of ether. The organic layer is separated and the aqueous layer is reextracted with 30 mL of ether. The combined organic layers are washed with 50 mL of water, dried over 10 g of anhydrous magnesium sulfate, and filtered. The residue is repeatedly washed with dry ether (3 × 20 mL). The solvent is removed on a rotary evaporator and the residue is dried to give a semi-solid that is purified by sublimation under vacuum to furnish 13.9–14.3 g (79–82%) of 1-trifluoromethyl-1-cyclohexanol as a white waxy solid, mp 60.8°C.