Dimethyl Sulfoxide → 4-Methyl-1,2-dithiolane-4-carboxylic acid

HRID 41810Notes

Reaction equation

HRID 41810 reaction equation
Cl[CH:2](Cl)[C:3]([CH3:8])(C)[C:4]([OH:6])=[O:5].C([O-])([O-])=O.[Na+].[Na+].C([O-])(=[S:18])C.[K+].C[S:22]([CH3:24])=O>O>[CH3:8][C:3]1([C:4]([OH:6])=[O:5])[CH2:24][S:22][S:18][CH2:2]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 10340Sodium Carbonate2×HCID 103039Propanoic acid, 3,3-dichloro-2,2-dimethyl-HCID 23670855Potassium ethanethioate

Product 1

HCID 200693114-Methyl-1,2-dithiolane-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

8 g of dichloropivalic acid are placed in a 250 ml three-necked flask on which is mounted a condenser and a dropping funnel. The acid is dissolved in 80 ml of water, slowly adding 4.6 g of Na2CO3. A solution of 10.7 g of potassium thioacetate is added dropwise and the reaction medium is brought to reflux. 14.9 g of Na2CO3 are added and the medium is again heated at reflux. After disappearance of the starting material, 7.3 ml of DMSO are added, followed by refluxing. The dithiolane is obtained after acidification by precipitation and drying of the solid under vacuum. A pale yellow solid is obtained.

Workup

  1. temperatureto reflux
  2. temperaturethe medium is again heated
  3. temperatureat reflux
  4. temperatureby refluxing

Sources & evidence

ORD record
ord-bb176405ee3c4692be973994088b8f98
Source dataset
uspto-grants-2013_09
Patent number
US08535647B2

Reaction notes

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