Dimethyl Sulfoxide → 2-(3-Chlorophenyl)oxirane

HRID 427048Notes

Reaction equation

HRID 427048 reaction equation
[H-].[Na+].CS(C)=O.[I-].[CH3:8][S+](C)C.[Cl:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH:16]=[O:17]>O.O1CCCC1>[Cl:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH:16]1[O:17][CH2:8]1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 114773-ChlorobenzaldehydeHCID 24758Sodium hydrideHCID 75127Trimethylsulfonium iodide

Product 1

HCID 1556132-(3-Chlorophenyl)oxirane

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 42.0 g. of 57% sodium hydride dispersed in oil and 700 ml. of dimethyl sulfoxide is stirred at 70°-75° C. for one to one and one-half hours. The solution is diluted with 700 ml. of dry tetrahydrofuran and cooled to 0° C., under nitrogen. A 200 g. (1.0 mole) sample of trimethylsulfonium iodide is added in portions, maintaining the temperature between 0°-5° C. The mixture is stirred for 15 minutes and then a solution of 70.4 g. (0.50 mole) of m-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 m-chlorostyrene oxide.

Workup

  1. additionA mixture of 42.0 g
  2. additionThe solution is diluted with 700 ml
  3. temperaturemaintaining the temperature between 0°-5° C
  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-4d2703a75b9a48b7ba6fc951811a30a0
Source dataset
uspto-grants-1979_10
Patent number
US04172890

Reaction notes

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