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

HRID 263113

Reaction equation

HRID 263113 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-7264d8d2c1274d419501d8848eafff6f
Source dataset
uspto-grants-1979_05
Patent number
US04156082

Linked notes

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