Diazomethane → 2-(4-Chlorobenzoyl)-2-(4-chlorophenyl)oxirane

HRID 329893

Reaction equation

HRID 329893 reaction equation
[N+](=C)=[N-].N(CN[C:8](N)=[O:9])=O.[OH-].[Na+].[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([C:22]([C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=2)=O)=[O:21])=[CH:16][CH:15]=1>CCOCC.O1CCOCC1>[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]([C:22]2([C:24]3[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=3)[CH2:8][O:9]2)=[O:21])=[CH:18][CH:19]=1

Participants

7

Reactant 4

HCID 9550DiazomethaneHCID 14798Sodium HydroxideHCID 189461,2-Ethanedione, 1,2-bis(4-chlorophenyl)-HCID 104823Urea, (nitrosomethyl)-

Product 1

HCID 198700842-(4-Chlorobenzoyl)-2-(4-chlorophenyl)oxirane

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

With cooling and stirring, an ethereal diazomethane solution prepared by reaction of 5.34 g of N-nitrosomethylurea with aqueous sodium hydroxide solution in ether is added dropwise to a solution of 5 g of 4,4'-dichlorobenzil in 50 ml of dioxane. When the dropwise addition is complete, stirring is continued for 16 hours at room temperature, and the reaction solution is then concentrated by evaporation. The residual oil is crude 2-(4-chlorobenzoyl)-2-(4-chlorophenyl)oxirane which is purified by high vacuum distillation.

Workup

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

Sources & evidence

ORD record
ord-057994b302f2495bbcf07f493a65ad1e
Source dataset
uspto-grants-1990_01
Patent number
US04894083

Linked notes

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