Sodium Methoxide → 2-Methoxy-3,3-dimethyl-2-(4-methylsulfanylphenyl)oxirane

HRID 1380596

Reaction equation

HRID 1380596 reaction equation
[CH3:1][O-:2].[Na+].Br[C:5]([CH3:17])([CH3:16])[C:6]([C:8]1[CH:13]=[CH:12][C:11]([S:14][CH3:15])=[CH:10][CH:9]=1)=[O:7]>CO>[CH3:16][C:5]1([CH3:17])[O:7][C:6]1([O:2][CH3:1])[C:8]1[CH:13]=[CH:12][C:11]([S:14][CH3:15])=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 114599841-Propanone, 2-bromo-2-methyl-1-[4-(methylthio)phenyl]-

Product 1

HCID 201925252-Methoxy-3,3-dimethyl-2-(4-methylsulfanylphenyl)oxirane

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

95.1 g (1.76 mols) of sodium methylate are dissolved in 600 ml of methanol, and 437.1 g (1.60 mols) of 2-bromo-2-methyl-1-[4-(methylthio)-phenyl]-propan-1-one, dissolved in 300 ml of methanol, are added dropwise to this solution at reflux temperature. The methanol is then removed by distillation. The residue is poured into ice water, and the mixture is extracted with diethyl ether. The ether solution is washed with water, dried over Na2SO4 and concentrated. The crystals obtained are purified by vacuum distillation.

Workup

  1. additionare added dropwise to this solution
  2. temperatureat reflux temperature
  3. customThe methanol is then removed by distillation
  4. additionThe residue is poured into ice water
  5. extractionthe mixture is extracted with diethyl ether
  6. washThe ether solution is washed with water
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated
  9. customThe crystals obtained
  10. distillationare purified by vacuum distillation

Sources & evidence

ORD record
ord-623991528b314e8bad08a3849278be8e
Source dataset
uspto-grants-1986_04
Patent number
US04582862

Linked notes

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