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

HRID 1401420Notes

Reaction equation

HRID 1401420 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)oxirane

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent

Procedure

To a solution of Trimethylsulfonium iodide (1-1.2 equiv.) in DMSO is added sodium hydride 60% dispersion in oil (1-1.8 equiv.) portionwise over 5 min. and stirred for 1 h at RT. A solution of 4-methylbenzaldehyde (1 equiv.) in DMSO is added to the reaction mixture dropwise over 20 min. and stirred at RT for 4 h. The reaction is monitored by TLC and the reaction mixture poured in water and extracted with EtOAc. The combined organic extract is washed with water, followed by brine, and dried over anhydrous sodium sulfate and evaporated to dryness to afford 2-p-tolyloxirane as crude product.

Workup

  1. stirringstirred at RT for 4 h
  2. extractionextracted with EtOAc
  3. extractionThe combined organic extract
  4. washis washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-a3f4794617e44d5a8db6fc7a056dff1b
Source dataset
uspto-grants-2014_12
Patent number
US08907097B2

Reaction notes

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