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

HRID 1401421Notes

Reaction equation

HRID 1401421 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

To a solution of trimethylsulfonium iodide (10.28 g, 50.37 mmol, 1.2 eq.) in DMSO (70 mL) was added sodium hydride 60% dispersion in oil (2.82 g, 70.5 mmol, 1.7 eq.) portionwise over 5 min. and stirred for an hour at RT. A solution of 4-methylbenzaldehyde (5.0 g, 42.0 mmol, 1 eq.) in DMSO (25 mL) was added to the reaction mixture dropwise over 20 min. It was stirred at RT for 4 h. TLC was checked and the reaction mixture was poured in 150 mL water and extracted with EtOAc. The combined organic extract was washed with water and brine. It was dried over anhydrous sodium sulfate and concentrated under vacuum to afford 5.2 g of 2-p-tolyloxirane as product. 1H NMR (CDCl3, free base) δ (ppm) 7.2-7.1 (m, 4H), 3.81-3.8 (t, 1H), 3.2-3.1 (m, 1H), 2.6-2.5 (m, 1H), 2.4 (s, 3H).

Workup

  1. stirringIt was stirred at RT for 4 h
  2. extractionextracted with EtOAc
  3. extractionThe combined organic extract
  4. washwas washed with water and brine
  5. dry with materialIt was dried over anhydrous sodium sulfate
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-cc2b95df375846209eeb04ab3a3c62c7
Source dataset
uspto-grants-2014_12
Patent number
US08907097B2

Reaction notes

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