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

HRID 867937Notes

Reaction equation

HRID 867937 reaction equation
[S:1]1(=[O:9])(=[O:8])[CH2:6][CH2:5][CH2:4][CH:3]([OH:7])[CH2:2]1.CC(C)=O.CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O>C(O)(C)C>[S:1]1(=[O:9])(=[O:8])[CH2:6][CH2:5][CH2:4][C:3](=[O:7])[CH2:2]1

Participants

5

Reactant 3

HCID 180AcetoneHCID 13567415Tetrahydro-2H-thiopyran-3-ol 1,1-dioxideHCID 131709961Jones' reagent

Product 1

HCID 11815935Dihydro-2H-thiopyran-3(4H)-one-1,1-dioxideYield 67.5%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-d266dfb256b7486bb2b480c2d3beb8b1
Source dataset
uspto-grants-1988_10
Patent number
US04777167

Reaction notes

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