p-Toluenesulfonic acid → 8-Thiabicyclo(3.2.1)octan-3-one

Participants

Reaction Steps

Tetrahydrothiopyran-4-one (19.1 g, 150 mmol), ethylene-1,2-diol (11.2 g. 180 mmol), toluene-p-sulfonic acid (0.5 g), and toluene (500 mL) was heated under reflux in a Dean-Stark apparatus for 1.5 h. The toluene was then removed by rotary evaporation, and the residue dissolved in ether and washed, first with 10% aqueous sodium hydroxide and then with water. The organic layer was dried (Na2SO4) and evaporated, and allowed to crystallize by standing in Et2O overnight, giving 24.4 g (93%) of the title compound.

Provenance & Evidence