Dimethyl Sulfide → 2-(2,4-Dichlorophenylethenyl)-2-(1-propylmercaptocyclopropyl) oxirane

HRID 1650734Notes

Reaction equation

HRID 1650734 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+]>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

6

Reactant 4

HCID 1068Dimethyl SulfideHCID 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-dichlorophenylethenyl 1-propylmercaptocyclopropyl ketone in 120 ml of tert.-butanol is first added to the reaction mixture with stirring and 39.1 g of potassium hydroxide powder are then introduced, while keeping the temperature of the reaction mixture at 20° to 30° C. The mixture is stirred at 30 C. for 3 hours more, then the dimethyl sulphide is removed 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 with water and concentrated by removing 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 reacted further without additional purification. ##STR73##

Workup

  1. customat 20° to 30° C
  2. stirringThe mixture is stirred at 30 C
  3. waitfor 3 hours more
  4. customthe dimethyl sulphide is removed under reduced pressure
  5. additionthe reaction mixture is then poured into 70 ml of a 1% strength aqueous hydrogen peroxide solution
  6. extractionThe mixture is extracted with ethyl acetate
  7. washThe organic phase is washed with water
  8. concentrationconcentrated
  9. customby removing the solvent under reduced pressure
  10. dry with materialafter drying over sodium sulphate

Sources & evidence

ORD record
ord-d8cfaa47d2b84e98a71a1b93c53aa898
Source dataset
uspto-grants-1990_05
Patent number
US04925865

Reaction notes

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