Menthol → 2-Isopropyl-5-methylcyclohexyl 4-methylbenzenesulfonate

Participants

Reaction Steps

7.8 g (0.05 mol) DL-menthol and 11.2 g (0.1 mol) 1,4-diazabicyclo[2.2.2]octane are added to 50 mL ethyl acetate. This solution is cooled in an ice bath and 14.3 g (0.075 mol) tosyl chloride in 30 mL ethyl acetate is added dropwise over 15 mins. The ice bath is removed and the mixture is allowed to stir at room temperature for 4 days. After this time the solid precipitate is filtered and washed. The ethyl acetate filtrate and washings are then combined and washed successively with 10% HCl, saturated aq NaHCO3 and brine. The ethyl acetate is then evaporated to yield 11.5 g (74%) of menthyl-p-toluenesulfonate.

Provenance & Evidence