Diazomethane → 2-(2,4-Dichlorobenzoyl)-2-(2,4-dichlorophenyl)oxirane

HRID 329892Notes

Reaction equation

HRID 329892 reaction equation
[N+](=C)=[N-].N(CN[C:8](N)=[O:9])=O.[OH-].[Na+].[Cl:13][C:14]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=1[C:21]([C:23]([C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][C:26]=1[Cl:32])=O)=[O:22]>CCOCC.O1CCOCC1>[Cl:13][C:14]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=1[C:21]([C:23]1([C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][C:26]=2[Cl:32])[CH2:8][O:9]1)=[O:22]

Participants

7

Reactant 4

HCID 9550DiazomethaneHCID 14798Sodium HydroxideHCID 104823Urea, (nitrosomethyl)-HCID 133916831,2-Bis(2,4-dichlorophenyl)ethane-1,2-dione

Product 1

HCID 198700832-(2,4-Dichlorobenzoyl)-2-(2,4-dichlorophenyl)oxirane

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

With cooling and stirring, an ethereal diazomethane solution prepared from 3.1 g of nitrosomethylurea and aqueous sodium hydroxide solution in ether is added dropwise to a solution of 3.4 g of 2,2',4,4'-tetrachlorobenzil in 50 ml of dioxane. When the dropwise addition is complete, stirring is continued for 16 hours at room temperature, and the reaction mixture is then concentrated to dryness. The residual oil is crude 2-(2,4-dichlorobenzoyl)-2-(2,4-dichlorophenyl)oxirane which is purified by high vacuum distillation.

Workup

  1. temperatureWith cooling
  2. additionWhen the dropwise addition
  3. stirringstirring
  4. concentrationthe reaction mixture is then concentrated to dryness
  5. distillationis purified by high vacuum distillation

Sources & evidence

ORD record
ord-4f354c660f6648798de6101459753803
Source dataset
uspto-grants-1990_01
Patent number
US04894083

Reaction notes

Loading…