2-Thiocresol → 1-(Cyclopropylsulfanyl)-2-methylbenzene

HRID 70563

Reaktionsgleichung

Reaktionsgleichung von HRID 70563
[CH3:1][C:2]([CH3:5])([O-])C.[K+].BrC1CC1.[CH3:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[SH:18]>CS(C)=O.[Cl-].[Na+].O>[CH:5]1([S:18][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[CH3:11])[CH2:2][CH2:1]1

Komponenten

6

Edukt 3

HCID 87122-ThiocresolHCID 78037BromocyclopropaneHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 579565761-(Cyclopropylsulfanyl)-2-methylbenzene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Potassium t-butoxide (994 mg) and bromocyclopropane (2.92 g) were added to a solution of 2-methylbenzenethiol (1.05 g) in dimethyl sulfoxide (10 mL), and the mixture was stirred at 100° C. for 9.5 hours. The reaction solution was cooled to room temperature and brine was added, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1) to give 1-(cyclopropylsulfanyl)-2-methylbenzene as an orange oil (1.41 g, quant.).

Aufarbeitung

  1. temperatureThe reaction solution was cooled to room temperature
  2. extractionfollowed by extraction with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent was then evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1)

Quellen und Nachweise

ORD-Eintrag
ord-53b183a844474fc5ab095796eb2aef6d
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822503B2

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