2-Chlorobenzaldehyde → 2-(2-Chlorophenyl)oxirane

HRID 1913861Notes

Reaction equation

HRID 1913861 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[I-].[CH3:11][S+](C)C.[OH-].[Na+]>ClCCl>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]1[CH2:11][O:5]1

Participants

5

Reactant 3

HCID 69962-ChlorobenzaldehydeHCID 14798Sodium HydroxideHCID 75127Trimethylsulfonium iodide

Product 1

HCID 5607092-(2-Chlorophenyl)oxirane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Chloro-benzaldehyde (5 mL, 44 mmol) was dissolved in dichloromethane (45 mL) and treated with trimethylsulfonium iodide (10.25 g, 49.28 mmol) and aqueous sodium hydroxide solution (50%, 44 g) subsequently. The mixture was stirred vigorously at room temperature for overnight. The organic phase was separated and concentrated to give clear oil, which was stored in the refrigerator and used directly without further purification.

Workup

  1. customThe organic phase was separated
  2. concentrationconcentrated
  3. customto give clear oil, which
  4. customused directly without further purification

Sources & evidence

ORD record
ord-dba1dc7e490d4ef0b8b6387862bb6d62
Source dataset
uspto-grants-2013_12
Patent number
US08609849B1

Reaction notes

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