Nitromethane → 4-Chloro-2-methyl-1-(2-nitrovinyl)benzene

HRID 510632Notes

Reaction equation

HRID 510632 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[C:4]([CH3:10])[CH:3]=1.Cl.CN.C([O-])(=O)C.[Na+].[N+:19]([CH3:22])([O-:21])=[O:20]>O.ClCCl>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[CH:22][N+:19]([O-:21])=[O:20])=[C:4]([CH3:10])[CH:3]=1

Participants

7

Reactant 4

HCID 6375NitromethaneHCID 517045Sodium AcetateHCID 27576584-Chloro-2-methylbenzaldehydeHCID 6364545Methylamine hydrochloride

Product 1

HCID 670259694-Chloro-2-methyl-1-(2-nitrovinyl)benzeneYield 94%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-chloro-2-methylbenzaldehyde (1.56 g, 10.1 mmol), methylamine hydrochloride (0.44 g, 6.5 mmol), and sodium acetate (0.53 g, 6.5 mmol) in nitromethane (4 mL) was vigorously stirred at ambient temperature for 24 hours. The reaction mixture was diluted with water (20 mL) and dichloromethane (40 mL). The organic layer was dried over sodium sulfate and evaporated to afford 4-chloro-2-methyl-1-(2-nitrovinyl)benzene as a light brown solid (1.87 g, 94% yield).

Workup

  1. dry with materialThe organic layer was dried over sodium sulfate
  2. customevaporated

Sources & evidence

ORD record
ord-ab36ae914539488985cc6db4e457eaf8
Source dataset
uspto-grants-2015_08
Patent number
US09096567B2

Reaction notes

Loading…