cis- (CAS NO.: ), which is also known as , 4-(1,1-dimethylethyl)-, cis-, could be produced through the following synthetic routes.

To a solution of 4.0 g. (0.012 mole) of iridium tetrachloride in 4.5 ml. of concentrated hydrochloric acid is added 180 ml. of water followed by 52 g. (50 ml., 0.42 mole) of trimethyl phosphite. This solution then is added to a solution of 30.8 g. (0.200 mole) of 4-tert-butylcyclohexanone in 635 ml. of 2-propanol contained in a 2-l. flask equipped with a reflux condenser. The solution is heated at reflux for 48 hours, at which time the 2-propanol is removed with a rotary evaporator. The remaining solution is diluted with 250 ml. of water and extracted with four 150-ml. portions of diethyl ether. The combined ether extracts are washed with two 100-ml. portions of water, which are combined with the aqueous residue, dried over magnesium sulfate or potassium carbonate, and concentrated on a rotary evaporator, yielding 29–31 g. (93–99%) of cis-4-tert-butylcyclohexanol as a white solid. Analysis of the crude product by GC shows it contains 95.8–96.2% cis-alcohol and 4.2–3.8% of the trans isomer with essentially no ketone remaining. Recrystallization from 40% aqueous ethanol affords greater than 99% pure cis-alcohol, m.p. 82–83.5° after sublimation.