Dimethyl Sulfoxide → 2-(3-Chlorophenyl)oxirane

HRID 2420084Notes

Reaction equation

HRID 2420084 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 1 to 11/2 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 4 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 4 hours
  5. extractionextracted with ether
  6. washThe extract is washed with brine
  7. customdried
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-bf4fcbd1d96e4696befe304594f8c362
Source dataset
uspto-grants-1978_08
Patent number
US04108989

Reaction notes

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