Dimethyl Sulfide → 2-(4-Iodophenyl)-2-methyloxirane

HRID 904233Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 904233
CSC.S([O:9][CH3:10])(OC)(=O)=O.[CH3:11][C:12]([C:14]1[CH:19]=[CH:18][C:17]([I:20])=[CH:16][CH:15]=1)=O.C[O-].[Na+]>C(#N)C>[I:20][C:17]1[CH:18]=[CH:19][C:14]([C:12]2([CH3:11])[CH2:10][O:9]2)=[CH:15][CH:16]=1

Komponenten

6

Edukt 4

HCID 1068Dimethyl SulfideHCID 6497Dimethyl SulfateHCID 728691-(4-Iodophenyl)ethan-1-oneHCID 10942334Sodium Methoxide

Produkt 1

HCID 233338282-(4-Iodophenyl)-2-methyloxiraneAusbeute 99,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel2×

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To a solution of 30 g of dimethyl sulfide in 30 ml of acetonitrile was added dropwise over a period of 30 minutes 30 g of dimethyl sulfate, while maintaining the temperature at 40° to 50° C., and the mixture was stirred for one hour at the same temperature. The reaction mixture was cooled to 25° C. and mixed with 30 g of 4-iodoacetophenone and 90 ml of acetonitrile. While stirring, 13.2 g of sodium methoxide was added to the mixture and stirring was continued for a further 30 minutes at room temperature to complete the reaction. Thereafter, the dimethyl sulfide and acetonitrile were removed by distillation, and to the residue were added 120 ml of cyclohexane and 120 ml of water, after which the mixture was thoroughly shaken. The organic layer was separated, dried over anhydrous magnesium sulfate, and freed from the solvent by distillation under reduced pressure to obtain 31.5 g (99% yield) of oily 2-(4-iodophenyl)-2-methyloxirane having a melting point of 44°-45° C.

Aufarbeitung

  1. temperaturewhile maintaining the temperature at 40° to 50° C.
  2. stirringWhile stirring
  3. stirringstirring
  4. waitwas continued for a further 30 minutes at room temperature
  5. customthe reaction
  6. customThereafter, the dimethyl sulfide and acetonitrile were removed by distillation
  7. additionto the residue were added 120 ml of cyclohexane and 120 ml of water
  8. stirringafter which the mixture was thoroughly shaken
  9. customThe organic layer was separated
  10. dry with materialdried over anhydrous magnesium sulfate
  11. distillationfreed from the solvent by distillation under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-975c4c8ded5a4cf8b32ea5624bac350c
Quelldatensatz
uspto-grants-1980_10
Patentnummer
US04230719

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