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

HRID 1915985Notes

Reaction equation

HRID 1915985 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. A pale yellow solid is obtained.

Workup

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

Sources & evidence

ORD record
ord-f96f56feecea45d791c77deec4322fcd
Source dataset
uspto-grants-2013_12
Patent number
US08617524B2

Reaction notes

Loading…