4-Methylbenzaldehyde → 2-(4-Methylphenyl)oxirane

HRID 1481378Notes

Reaction equation

HRID 1481378 reaction equation
[I-].[CH3:2][S+](C)C.[H-].[Na+].[CH3:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][CH:10]=1>CS(C)=O.O>[C:9]1([CH3:8])[CH:16]=[CH:15][C:12]([CH:13]2[CH2:2][O:14]2)=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 77254-MethylbenzaldehydeHCID 24758Sodium hydrideHCID 75127Trimethylsulfonium iodide

Product 1

HCID 1081112-(4-Methylphenyl)oxiraneYield 92.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent

Procedure

The title compound was prepared by following general procedure 3. To a solution of trimethylsulfonium iodide (10.28 g, 50.37 mmol, 1.2 equiv.) in DMSO (70 mL) was added sodium hydride 60% dispersion in oil (2.82 g, 70.5 mmol, 1.7 equiv.) portionwise over 5 min. and stirred for 1 h at RT. A solution of 4-methylbenzaldehyde (5.0 g, 42.0 mmol, 1 equiv.) in DMSO (25 mL) was added to the reaction mixture dropwise over 20 min. It was stirred at RT for 4 h. The reaction mixture was checked by TLC and the reaction mixture was poured in water (150 mL) and extracted with ethyl acetate. The combined organic extract was washed with water and brine and dried over anhydrous sodium sulfate and evaporated to dryness to afford 2-p-tolyloxirane (5.2 g).

Workup

  1. customThe title compound was prepared
  2. stirringIt was stirred at RT for 4 h
  3. extractionextracted with ethyl acetate
  4. extractionThe combined organic extract
  5. washwas washed with water and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-8396d1f857c34bf799cfe0837413a9d9
Source dataset
uspto-grants-2016_08
Patent number
US09409910B2

Reaction notes

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