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

HRID 41131Notes

Reaction equation

HRID 41131 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 are mounted a condenser and a dropping funnel. The acid is dissolved in 80 ml of water, and 4.6 g of Na2CO3 are slowly added. 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 refluxed. After disappearance of the starting material, 7.3 ml of DMSO are added, followed by refluxing. The dithiolane is obtained after acidification by precipitating and drying the solid under vacuum.

Workup

  1. temperatureto reflux
  2. temperaturethe medium is again refluxed
  3. temperatureby refluxing

Sources & evidence

ORD record
ord-50891be04e104c3b9b3543f1b078e9b2
Source dataset
uspto-grants-2013_09
Patent number
US08530511B2

Reaction notes

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