2-Methylbenzaldehyde → 2-(2-Methylphenyl)oxirane

HRID 1706136Notes

Reaction equation

HRID 1706136 reaction equation
[H-].[Na+].[I-].[CH3:4][S+](C)C.[C:8]1([CH3:16])[C:9]([CH:14]=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=1>CCCCCC.C1COCC1.CS(C)=O>[CH3:16][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH:14]1[O:15][CH2:4]1

Participants

7

Reactant 3

HCID 107222-MethylbenzaldehydeHCID 24758Sodium hydrideHCID 75127Trimethylsulfonium iodide

Product 1

HCID 1510422-(2-Methylphenyl)oxiraneYield 83%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolvent2×HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

Sodium hydride (57%) (4.84 g., 0.115 mole) previously washed with hexane was stirred with dry dimethylsulfoxide (70 ml) at 65°-70° for 2 hours under argon. The mixture was diluted with dry THF (70 ml), cooled to -5° and trimethylsulfonium iodide (23.5 g, 0.115 mole) in 100 ml of dry DMSO was added over a period of 3 minutes. After stirring for one minute o-tolualdehyde (11.5 g, 0.0926 mole) was added at a moderate rate while keeping the reaction mixture at 0° to -5°. The mixture was stirred at 0° for 5 minutes and at room temperature for 1 hour, diluted with 500 ml of ice water and extracted three times with ether. The ether solution was washed with saturated sodium chloride, dried with sodium sulfate and evaporated to an oil which was distilled under reduced pressure (~0.25-0.50 mm) to give 10.25 g (83 %) of o-methylstyrene oxide as a clear liquid (b.p. 35°-38°).

Workup

  1. temperaturecooled to -5°
  2. additionwas added at a moderate rate
  3. customat 0° to -5°
  4. extractionextracted three times with ether
  5. washThe ether solution was washed with saturated sodium chloride
  6. dry with materialdried with sodium sulfate
  7. customevaporated to an oil which
  8. distillationwas distilled under reduced pressure (~0.25-0.50 mm)

Sources & evidence

ORD record
ord-91ef493f1acd45b594e9f60eecf85733
Source dataset
uspto-grants-1980_06
Patent number
US04206210

Reaction notes

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