Benzenepropanal → 2-(2-Phenylethyl)oxirane

HRID 2072188Notes

Reaction equation

HRID 2072188 reaction equation
[I-].[CH3:2][S+](C)(C)=O.[H-].[Na+].[H][H].[C:11]1([CH2:17][CH2:18][CH:19]=[O:20])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>CS(C)=O.O.C(OCC)(=O)C>[O:20]1[CH:19]([CH2:18][CH2:17][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:2]1

Participants

8

Reactant 4

HCID 7707BenzenepropanalHCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 178418361HCID 178418361, compound

Product 1

HCID 1359552-(2-Phenylethyl)oxirane

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of trimethyloxosulphonium iodide (2.64 g.) in dry dimethylsulphoxide (50 ml. ) is stirred at 50°-60° C. in an atmosphere of nitrogen and an 80% w/w mineral oil dispersion of sodium hydride (0.36 g.) is added. Stirring and heating are continued until the solution is clear and no more hydrogen is evolved. A solution of 3-phenylpropionaldehyde (1.34 g.) in dry dimethyl sulphoxide (10 ml.) is added and the mixture is stirred at 50°-60° C. in an atmosphere of nitrogen for 3 hours. The mixture is cooled and diluted with water (200 ml.), and the product is obtained by extraction with ethyl acetate (3 × 80 ml.). Removal of the solvent from the combined extracts gives 1,2-epoxy-4-phenylbutane as an oil which is not further purified.

Workup

  1. temperatureheating
  2. stirringthe mixture is stirred at 50°-60° C. in an atmosphere of nitrogen for 3 hours
  3. temperatureThe mixture is cooled
  4. customRemoval of the solvent from the combined extracts

Sources & evidence

ORD record
ord-d49898de66144aa1bd1e8a5939238b9a
Source dataset
uspto-grants-1977_09
Patent number
US04049808

Reaction notes

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