Dimethyl Sulfoxide → 2-(4-Methoxyphenyl)oxirane

HRID 2420088Notes

Reaction equation

HRID 2420088 reaction equation
[H-].[Na+].CS(C)=O.[I-].[CH3:8][S+](C)C.[CH3:12][O:13][C:14]1[CH:21]=[CH:20][C:17]([CH:18]=[O:19])=[CH:16][CH:15]=1>O.O1CCCC1>[CH3:12][O:13][C:14]1[CH:21]=[CH:20][C:17]([CH:18]2[O:19][CH2:8]2)=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 24758Sodium hydrideHCID 312444-MethoxybenzaldehydeHCID 75127Trimethylsulfonium iodide

Product 1

HCID 980482-(4-Methoxyphenyl)oxirane

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-5 °C

Procedure

A suspension of 4.84 g. of sodium hydride (57% mineral oil dispersion) in 70 ml. of dry dimethyl sulfoxide is heated at about 65° C. under argon with stirring for 1 hour. Dry tetrahydrofuran (75 ml.) is added and the resulting solution is cooled to -5° C. Trimethylsulfonium iodide (19 g., 92.8 mmole) is added very slowly and stirring is continued for about 5 minutes. A solution of 12.6 g. (92.8 mmole) of p-methoxybenzaldehyde in 120 ml. of tetrahydrofuran is added and the temperature is maintained at -5° C. After addition is completed the mixture is allowed to warm to room temperature, poured into water and extracted with ether. The extract is washed with saturated sodium chloride solution, dried and evaporated to give p-methoxystyrene oxide.

Workup

  1. additionA suspension of 4.84 g
  2. stirringstirring
  3. waitis continued for about 5 minutes
  4. temperaturethe temperature is maintained at -5° C
  5. additionAfter addition
  6. temperatureto warm to room temperature
  7. extractionextracted with ether
  8. washThe extract is washed with saturated sodium chloride solution
  9. customdried
  10. customevaporated

Sources & evidence

ORD record
ord-10b8aa1feac5449a8dae0b650a192b29
Source dataset
uspto-grants-1978_08
Patent number
US04108989

Reaction notes

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