Dimethyl Sulfoxide → 2-(2-Chlorophenyl)oxirane

HRID 971608Notes

Reaction equation

HRID 971608 reaction equation
[OH-].[Na+].CS(C)=O.[I-].[CH3:8][S+](C)C.[Cl:12][C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[CH:15]=[O:16]>O1CCCC1.O>[Cl:12][C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[CH:15]1[O:16][CH2:8]1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 69962-ChlorobenzaldehydeHCID 14798Sodium HydroxideHCID 75127Trimethylsulfonium iodide

Product 1

HCID 5607092-(2-Chlorophenyl)oxirane

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 42.0 g of 57% sodium hydroxide dispersed in oil and 700 ml of dimethyl sulfoxide is stirred at 70°-75° for one to one and one-half hours. The solution in diluted with 700 ml of dry tetrahydrofuran and cooled to 0°, under nitrogen. A 200 g of (1.0 mol) sample of trimethylsulfonium iodide is added in portions, maintaining the temperature between 0°-5°. The mixture is stirred for 15 minutes and then a solution of 70.4 g (0.50 mol) of o-chlorobenzaldehyde in 300 ml of dry tetrahydrofuran is added dropwise. The resulting mixture is stirred at room temperature for four hours, poured into water and extracted with ether. The extract is washed with brine, dried and evaporated in vacuo to leave o-chlorostyrene oxide.

Workup

  1. temperaturecooled to 0°, under nitrogen
  2. temperaturemaintaining the temperature between 0°-5°
  3. stirringThe mixture is stirred for 15 minutes
  4. stirringThe resulting mixture is stirred at room temperature for four hours
  5. extractionextracted with ether
  6. washThe extract is washed with brine
  7. customdried
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-a36a35e735b74d50bbb081ea7050e35c
Source dataset
uspto-grants-1979_07
Patent number
US04160765

Reaction notes

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