Acetone → Dihydro-2H-thiopyran-3(4H)-one-1,1-dioxide
Reaction equation
[CH3:1][C:2]([CH3:4])=[O:3].C[C:6]([CH3:8])=O.[OH:9][S:10](O)(=O)=[O:11].O=[Cr](=O)=O>C(O)(C)C>[S:10]1(=[O:11])(=[O:9])[CH2:6][CH2:8][CH2:4][C:2](=[O:3])[CH2:1]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of tetrahydrothiopyran-3-o1-1,1-dioxide (7.5 g, 0.05 moles) and acetone (150 mL) was slowly added enough Jones reagent to maintain a brown color for at least 10 minutes without need for additional reagent. The excess reagent was reduced by addition of isopropanol (5 mL). The mixture was filtered through anhydrous magnesium sulfate and the chromium salts were washed 3× with acetone. The solvent was removed in vacuo to give a solid which was triturated with ethanol. The resulting crystals were isolated by filtration and rinsed 3× with diethyl ether. After drying, 5.0 g of product was obtained. H' NMR CDCl3 4.0 (singlet, 2H) 3.3 (triplet, 2H) 2.6 (triplet, 2H) 2.3 (multiplet, 2H).