Hydrogen Peroxide → HCID 14403426, compound

HRID 1089892Notes

Reaction equation

HRID 1089892 reaction equation
CSC.S([O:9][CH3:10])(OC)(=O)=O.[C:11]1([S:17][C:18]2([C:21]([CH2:23][CH2:24][C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=3)=O)[CH2:20][CH2:19]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[OH-].[K+].OO>C(O)(C)(C)C>[Cl:31][C:28]1[CH:29]=[CH:30][C:25]([CH2:24][CH2:23][C:21]2([C:18]3([S:17][C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=4)[CH2:20][CH2:19]3)[CH2:10][O:9]2)=[CH:26][CH:27]=1

Participants

7

Reactant 5

HCID 784Hydrogen PeroxideHCID 1068Dimethyl Sulfide2×HCID 6497Dimethyl SulfateHCID 14797Potassium HydroxideHCID 14403425HCID 14403425, compound

Product 1

HCID 14403426HCID 14403426, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent2×

Procedure

21 ml (0.29 mol) of dimethyl sulphide and 32.5 g (0.26 mol) of dimethyl sulphate are added to 40 ml of tert.-butanol and the mixture is allowed to stand at room temperature for 14 hours. A solution of 30 g (0.095 mol) of 4-chlorophenylethyl 1-phenylmercapto-cyclopropyl ketone in 90 ml of tert.-butanol is initially added dropwise to the reaction mixture with stirring and 29.2 g of potassium hydroxide powder are then 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, 25.6 g (82% of theory) of 2-(4-chlorophenylethyl)-2-(1-phenylmercapto-cyclopropyl)-oxirane are obtained in the form of an oily product, which is further reacted without additional purification. ##STR72##

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-d49ad6948d844f49b7280740eeae1a77
Source dataset
uspto-grants-1992_01
Patent number
US05079374

Reaction notes

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