Hydrogen Peroxide → 2-(2,4-Dichlorophenylethenyl)-2-(1-propylmercaptocyclopropyl) oxirane

HRID 1650595Notes

Reaction equation

HRID 1650595 reaction equation
CSC.S([O:9][CH3:10])(OC)(=O)=O.[CH2:11]([S:14][C:15]1([C:18]([CH:20]=[CH:21][C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=2[Cl:29])=O)[CH2:17][CH2:16]1)[CH2:12][CH3:13].[OH-].[K+].OO>C(O)(C)(C)C>[Cl:29][C:23]1[CH:24]=[C:25]([Cl:28])[CH:26]=[CH:27][C:22]=1[CH:21]=[CH:20][C:18]1([C:15]2([S:14][CH2:11][CH2:12][CH3:13])[CH2:16][CH2:17]2)[CH2:10][O:9]1

Participants

7

Reactant 5

HCID 784Hydrogen PeroxideHCID 1068Dimethyl Sulfide2×HCID 6497Dimethyl SulfateHCID 14797Potassium HydroxideHCID 54332237HCID 54332237, compound

Product 1

HCID 540874812-(2,4-Dichlorophenylethenyl)-2-(1-propylmercaptocyclopropyl) oxiraneYield 91%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent2×

Procedure

30 ml (0.41 mol) of dimethyl sulphide and 43.5 g (0.35 mol) of dimethyl sulphate are added to 60 ml of tert.-butanol and allowed to stand at room temperature for 14 hours. A solution of 40 g (0.13 mol) of 2,4-dichlorophenyl-ethenyl 1-propylmercaptocyclopropyl ketone in 120 ml of tert.-butanol is initially added dropwise to the reaction mixture with stirring and then 39.1 g of potassium hydroxide powder is introduced, the temperature of the reaction mixture being held at 20° to 30° C. The mixture is stirred for a further 3 hours at 30° C., then the dimethyl sulphide is stripped off under reduced pressure and the reaction mixture is then poured into 70 ml of a 1% strength aqueous hydrogen peroxide solution. The mixture is extracted with ethyl acetate. The organic phase is washed using water and concentrated by stripping off the solvent under reduced pressure after drying over sodium sulphate. In this manner, 38.2 g (91% of theory) of 2-(2,4-dichlorophenylethenyl)-2-(1-propylmercaptocyclopropyl)-oxirane are obtained in the form of an oily product, which is further reacted without additional purification. ##STR77##

Workup

  1. custombeing held at 20° to 30° C
  2. stirringThe mixture is stirred for a further 3 hours at 30° C.
  3. extractionThe mixture is extracted with ethyl acetate
  4. washThe organic phase is washed
  5. concentrationconcentrated
  6. dry with materialafter drying over sodium sulphate

Sources & evidence

ORD record
ord-37acef85022c4b678141d2f35ee35fa9
Source dataset
uspto-grants-1990_05
Patent number
US04925482

Reaction notes

Loading…