Sodium Chloride → 3,3-Dimethyl-1-tert.-butylthio-2-butanone

HRID 436919Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 436919
[Na].[CH3:2][C:3]([SH:6])([CH3:5])[CH3:4].Br[CH2:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11].[Cl-].[Na+]>C(O)C.O>[CH3:11][C:10]([CH3:13])([CH3:12])[C:9](=[O:14])[CH2:8][S:6][C:3]([CH3:5])([CH3:4])[CH3:2]

Komponenten

7

Edukt 4

HCID 5234Sodium ChlorideHCID 6387tert-Butyl mercaptanHCID 21642BromopinacoloneHCID 5360545Sodium

Produkt 1

HCID 233496733,3-Dimethyl-1-tert.-butylthio-2-butanone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of 5.8 g (0.25 mol) of sodium metal in 175 ml of absolute ethanol is added, dropwise, 24.4 g (0.27 mol) of 2-methyl-2-propanethiol. The stirred solution is heated for 20 minutes, cooled, and treated in a dropwise manner with 44.8 g (0.25 mol) of 1-bromopinacolone, prepared according to the procedure of J. Am. Chem. Soc., 74, 4507 (1952). This reaction mixture is heated at reflux for 20 minutes, cooled, and poured onto 200 g of ice and water. After being saturated with sodium chloride, the mixture is extracted with four portions of ether. The combined ether extracts are dried over anhydrous magnesium sulfate, filtered, and stripped of solvent. Distillation of the residue through a short Vigreaux column gives the desired product. Properties of this, and similar compounds prepared by substantially the same procedure using the appropriate mercaptans and -haloketones, are given in Table 1.

Aufarbeitung

  1. temperatureThe stirred solution is heated for 20 minutes
  2. temperaturecooled
  3. customprepared
  4. temperatureThis reaction mixture is heated
  5. temperatureat reflux for 20 minutes
  6. temperaturecooled
  7. extractionthe mixture is extracted with four portions of ether
  8. dry with materialThe combined ether extracts are dried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. distillationDistillation of the residue through a short Vigreaux column

Quellen und Nachweise

ORD-Eintrag
ord-471a53b877ac4eddbc0b6b95b8c2e515
Quelldatensatz
uspto-grants-1977_06
Patentnummer
US04028413

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