cis- (CAS no.: ) could be produced as the following synthetic routes.

A. N-oxide. A 100-ml., three-necked, round-bottomed flask equipped with a reflux condenser, a magnetic stirring bar, and a dropping funnel is flushed with nitrogen or argon and charged with 32.3 g. (35.1 ml., 0.320 mole) of N-methylmorpholine. The flask is immersed in an oil bath maintained at 75°, and 32.4 g. (29.1 ml., 0.286 mole) of 30% aqueous hydrogen peroxide is added dropwise over a period of 2.5 hours. The mixture is stirred for 20 hours at 75°, at which time a negative peroxide test (potassium iodide paper) is obtained. The reaction mixture is cooled to 50°, and a slurry of 50 ml. of methanol, 0.5 g. of charcoal, and 0.5 g. of Celite is added. After being stirred for 1 hour, the mixture is filtered and the filter cake washed with three 15-ml. portions of methanol. The filtrate and combined washings are concentrated with a rotary evaporator (water aspirator vacuum), with the bath temperature finally reaching 95°, where it is held for 10 minutes. The flask is fitted with a reflux condenser, and the residual viscous oil is dissolved in 25 ml. of acetone at 60°. On cooling to 40° (with seeding, if crystals of the N-oxide are available) the product spontaneously crystallizes. The slurry is stored at room temperature overnight, cooled in an ice bath, and filtered. The crystals are washed with three 15-ml. portions of 0° acetone and dried overnight at 40° (0.01 mm.) The yield of colorless crystalline monohydrate is 32.4–34.3 g. (83.8–88.7%), m.p. 75–76°.

B. cis-1,2-Cyclohexanediol. A 250-ml., three-necked, round-bottomed flask, with a magnetic stirrer and a nitrogen inlet, is charged with 14.81 g. (0.1097 mole) of monohydrate, 40 ml. of water, and 20 ml. of acetone. To this solution is added ca. 70 mg. of osmium tetroxide (0.27 mmole) and 8.19 g. (10.1 ml., 0.100 mole) of cyclohexene. This two-phase solution is stirred vigorously under nitrogen at room temperature. The reaction is slightly exothermic and is maintained at room temperature with a water bath. During the overnight stirring period, the reaction mixture becomes homogeneous and light brown in color. After 18 hours, TLC shows the reaction to be complete. hydrosulfite (0.5 g.) and 5 g. of Magnesol slurried in 20 ml. of water are added, the slurry is stirred for 10 minutes, and the mixture is filtered through a pad of 5 g. of Celite on a 150-ml. sintered-glass funnel. The Celite cake is washed with three 15-ml. portions of acetone. The filtrate, combined with acetone wash, is neutralized to pH 7 with 6.4 ml. of 12 N sulfuric acid. The acetone is evaporated under vacuum using a rotary evaporator. The pH of the resulting aqueous solution is adjusted to pH 2 with 2.3 ml. of 12 N sulfuric acid, and the cis-diol is separated from N-methylmorpholine hydrosulfate by extraction with five 45-ml. portions of n-butanol. The combined butanol extracts are extracted once with 25 ml. of 25% sodium chloride solution, and the aqueous phase is backwashed with 50 ml. of butanol. The butanol extracts are evaporated under vacuum, giving 12.1 g. of white solid. The cis-diol is separated from a small amount of insoluble material (ca. 0.7 g.) by boiling the solid with a 200-ml., an 80-ml., and a 20-ml. portion of , decanting the solvent each time. The combined ether fractions are evaporated to ca. 50 ml. under vacuum, and crystalline white plates precipitate. The mixture is cooled to ca. -15°. The crystals are filtered, washed with two 10-ml. portions of cold diisopropyl ether, and dried, yielding 10.18–10.32 g. (89–90%) of the cis-diol (m.p. 96–97°).