Dimethyl Sulfoxide → 2-(Tert-Butylthio)Benzaldehyde

HRID 1681284Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1681284
[OH-].[K+].[C:3]([SH:7])([CH3:6])([CH3:5])[CH3:4].CS(C)=O.Cl[C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[CH:15]=[O:16]>O.C(OCC)(=O)C>[CH3:4][C:3]([CH3:6])([S:7][C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[CH:15]=[O:16])[CH3:5]

Komponenten

7

Edukt 4

HCID 679Dimethyl SulfoxideHCID 6387tert-Butyl mercaptanHCID 69962-Chlorobenzaldehyde2×HCID 14797Potassium Hydroxide

Produkt 1

HCID 27769202-(Tert-Butylthio)Benzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

Powdered potassium hydroxide (21.9 g, 390 mmol) and 56 ml (497 mmol) of terbutyl mercaptan were mixed 55.5 ml of dimethylsulfoxide in a 250 ml three-neck flask. To this stirred mixture was added dropwise over a ten minute period 50 g (356 mmol) of 2-chloro-benzaldehyde. During addition of the 2-chlorobenzaldehyde, the reaction mixture warmed to 120° C. After addition was complete, the mixture was allowed to react at about 110° C. for 1.5 hours. At the end of this time, the mixture was cooled to room temperature and taken up on 600 ml of ethyl acetate and 1 liter of water. The organic layer was separated, dried and evaporated to yield 2-(1,1-dimethylethylthio)benzaldehyde, b.p. 80°-82° C. at 0.05 mm Hg, which was used without further purification in the next step of the process.

Aufarbeitung

  1. additionAfter addition
  2. customto react at about 110° C. for 1.5 hours
  3. temperatureAt the end of this time, the mixture was cooled to room temperature
  4. customThe organic layer was separated
  5. customdried
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-499b8e0952bc4cb891027bfb4f45409b
Quelldatensatz
uspto-grants-1992_12
Patentnummer
US05169961

Notizen zur Reaktion

Wird geladen…