Sulfuric Acid → Nsc62660

Participants

Reaction Steps

Ten grams (86 mmol) of trans-1,2-cyclohexanediol (CAS No. 1460-57-7) was added to toluene, and 10 g (84 mmol) of thionyl chloride was added dropwise thereto for reaction. The resulting solution was distilled. A cyclohexanediol cyclic sulfite (trans isomer) was recovered with a yield of 90%. Next, a methylene chloride solution containing 10 g (62 mmol) of cyclohexanediol cyclic sulfite was mixed with 180 g of 10% sulfuric acid aqueous solution. The mixture was mixed with 11 g (70 mmol) of potassium permanganate in an ice bath for reaction. Thereafter, the excess amount of potassium permanganate was neutralized by sodium hydrogen sulfite. The solvent was then distilled away from the organic layer. The solid product was crystallized with diethyl ether. A purified hexahydro-1,3,2-benzodioxathiol-2,2-dioxide (trans isomer) was recovered with a yield of 24%.

Provenance & Evidence