Sodium Hydroxide → 1-Methoxy-3-(3-methylbut-2-enylsulphanyl)benzene

HRID 22994

Reaktionsgleichung

Reaktionsgleichung von HRID 22994
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([SH:9])[CH:6]=[CH:7][CH:8]=1.[OH-].[Na+].[CH3:12][C:13](=[CH:15][CH2:16]Br)[CH3:14]>CC(C)=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([S:9][CH2:16][CH:15]=[C:13]([CH3:14])[CH3:12])[CH:4]=1

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 700922-Butene, 1-bromo-3-methyl-HCID 849893-Methoxybenzenethiol

Produkt 1

HCID 225925921-Methoxy-3-(3-methylbut-2-enylsulphanyl)benzeneAusbeute 90,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel2×

Versuchsvorschrift

50.45 g (360.0 mmol) of 3-methoxythiophenol, 360 ml of acetone and 14.40 g (360.0 mmol) of sodium hydroxide pellets are introduced into a one liter round-bottomed flask under a nitrogen atmosphere and the mixture is heated at reflux for three hours. A solution composed of 53.6 g (360.0 mmol) of 2-methyl-4-bromo-2-butene and of 60 ml of acetone is added dropwise. Reflux is maintained for sixteen hours and the reaction mixture is evaporated to dryness. Water is added, extraction is carried out with ethyl acetate, the organic phase is washed with water and then using a saturated sodium chloride solution, dried over magnesium sulphate and filtered, and the solvents are evaporated. The residue obtained is distilled under reduced pressure (5×10−2 bar/113° C.) to produce 67.81 g (90%) of the expected compound in the form or a pale-yellow oil.

Aufarbeitung

  1. temperaturethe mixture is heated
  2. temperatureat reflux for three hours
  3. additionis added dropwise
  4. temperatureReflux
  5. temperatureis maintained for sixteen hours
  6. customthe reaction mixture is evaporated to dryness
  7. additionWater is added
  8. extractionextraction
  9. washthe organic phase is washed with water
  10. dry with materialdried over magnesium sulphate
  11. filtrationfiltered
  12. customthe solvents are evaporated
  13. customThe residue obtained
  14. distillationis distilled under reduced pressure (5×10−2 bar/113° C.)

Quellen und Nachweise

ORD-Eintrag
ord-b12277d88d5544d0af86d992556ac845
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06849658B2

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