Dichloromethane → 1,3,2-Dioxathiane, 5,5-dimethyl-, 2,2-dioxide

HRID 1982583Notes

Reaction equation

HRID 1982583 reaction equation
[CH3:1][C:2]1([CH3:9])[CH2:7][O:6][S:5](=[O:8])[O:4][CH2:3]1.C(Cl)Cl.[O-:13][Mn](=O)(=O)=O.[K+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O>[CH3:1][C:2]1([CH3:9])[CH2:7][O:6][S:5](=[O:13])(=[O:8])[O:4][CH2:3]1

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 516875Potassium PermanganateHCID 108772941003-85-6

Product 1

HCID 1205561,3,2-Dioxathiane, 5,5-dimethyl-, 2,2-dioxideYield 129.2%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolvent

Procedure

10 g (0.067 mol) of 5,5-dimethyl-1,3,2-dioxathiane 2-oxide (prepared in accordance with Example 1), 70 ml of methylene chloride, 0.76 g (0.0033 mol) of benzyltriethylammonium chloride and 70 ml of water are placed in a 350 ml four-necked flask which is provided with a stirrer and a thermometer. 7.5 g (0.0475 mol) of KMnO4 are added portion-wise at 5°-10° C. and while stirring vigorously. After the addition the reaction mixture is stirred at room temperature for a further 30 minutes and suction filtered. The organic phase is separated. The residue is washed well on the suction filter with 20 ml of methylene chloride and the aqueous phase is again extracted with this new filtrate. The combined organic phases are extracted with 1 g of NaHSO3 in 20 ml of water and washed with a small amount of water. After drying over Na2SO4 and evaporation there are obtained 10.2 g of 5,5-dimethyl-1,3,2-dioxathiane 2,2-dioxide as a white powder with a m.p. of 80°-82° C.

Workup

  1. customwhich is provided with a stirrer
  2. additionAfter the addition the reaction mixture
  3. stirringis stirred at room temperature for a further 30 minutes
  4. filtrationsuction filtered
  5. customThe organic phase is separated
  6. washThe residue is washed well on the suction
  7. filtrationfilter with 20 ml of methylene chloride
  8. extractionthe aqueous phase is again extracted with this new filtrate
  9. extractionThe combined organic phases are extracted with 1 g of NaHSO3 in 20 ml of water
  10. washwashed with a small amount of water
  11. dry with materialAfter drying over Na2SO4 and evaporation there

Sources & evidence

ORD record
ord-a4a55b31d87945f88cd8a8165db133d4
Source dataset
uspto-grants-1986_06
Patent number
US04596879

Reaction notes

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