Methanethiol → 2-Methylthio-2,4-dimethylpentan-3-one

HRID 462850

Reaction equation

HRID 462850 reaction equation
CO.[Na].[CH3:4][SH:5].Br[C:7]([CH3:14])([C:9](=[O:13])[CH:10]([CH3:12])[CH3:11])[CH3:8]>O>[CH3:4][S:5][C:7]([CH3:14])([C:9](=[O:13])[CH:10]([CH3:12])[CH3:11])[CH3:8]

Participants

6

Reactant 4

HCID 878MethanethiolHCID 887MethanolHCID 2225752-Bromo-2,4-dimethylpentan-3-oneHCID 5360545Sodium

Product 1

HCID 132479432-Methylthio-2,4-dimethylpentan-3-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 200 ml. of methanol containing 9.2 g. (0.40 mole) sodium metal was cooled in an ice-bath and saturated with gaseous methyl mercaptan. To this was added 77.2 g. (0.40 mole) of 2-bromo-2,4-dimethylpentan-3-one at room temperature and the resulting mixture stirred for two hours. The reaction mixture was diluted with water, extracted with ethyl ether, the extracts washed with water, brine and dried over anhydrous sodium sulfate. The ether was evaporated and the residue distilled in vacuo to afford 50.4 g. of product, B.P. 76° (20 mm.).

Workup

  1. additionTo this was added 77.2 g
  2. extractionextracted with ethyl ether
  3. washthe extracts washed with water, brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe ether was evaporated
  6. distillationthe residue distilled in vacuo
  7. customto afford 50.4 g

Sources & evidence

ORD record
ord-a6d115f7e03444bbbc028a8a375c64ed
Source dataset
uspto-grants-1985_05
Patent number
US04517379

Linked notes

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