Acetone → Dihydro-2H-thiopyran-3(4H)-one-1,1-dioxide

To a solution of tetrahydrothiopyran-3-ol-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).

1. temperatureto maintain a brown color for at least 10 minutes without need for additional reagent
2. filtrationThe mixture was filtered through anhydrous magnesium sulfate
3. washthe chromium salts were washed 3× with acetone
4. customThe solvent was removed in vacuo
5. customto give a solid which
6. customwas triturated with ethanol
7. customThe resulting crystals were isolated by filtration
8. washrinsed 3× with diethyl ether
9. customAfter drying

ORD record

ord-753f7b58542840c384b0fe9ee4159068

Source dataset

uspto-grants-1989_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04845225