Nitromethane → 2-Chloro-3,4-dimethoxy-1-[(E)-2-nitroethenyl]benzene

HRID 525842Notes

Reaction equation

HRID 525842 reaction equation
[Cl:1][C:2]1[C:9]([O:10][CH3:11])=[C:8]([O:12][CH3:13])[CH:7]=[CH:6][C:3]=1[CH:4]=O.[N+:14]([CH3:17])([O-:16])=[O:15].C([O-])(=O)C.[NH4+]>C(O)(=O)C.[Cl-].[Na+].O>[Cl:1][C:2]1[C:9]([O:10][CH3:11])=[C:8]([O:12][CH3:13])[CH:7]=[CH:6][C:3]=1/[CH:4]=[CH:17]/[N+:14]([O-:16])=[O:15]

Participants

6

Reactant 3

HCID 6375NitromethaneHCID 794452-ChloroveratraldehydeHCID 517165Ammonium Acetate

Product 1

HCID 130518862-Chloro-3,4-dimethoxy-1-[(E)-2-nitroethenyl]benzeneYield 100%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

The mixture of 2-chloro-3,4-dimethoxybenzaldehyde (5 g, 24.92 mmol) (Aldrich) and nitromethane (6.6 ml, 122 mmol) and ammonium acetate (1.921 g, 24.92 mmol) was reflux in glacial acetic acid (20 mL) for 4 h. Mixture was diluted with brine (300 ml) and extracted with ethyl acetate (2×150 ml), washed with water, dried over magnesium sulfate and evaporated to give (E)-2-chloro-3,4-dimethoxy-1-(2-nitrovinyl)benzene (6.07 g, 24.92 mmol, 100% yield). LCMS (M+H)+: 244.0

Workup

  1. extractionextracted with ethyl acetate (2×150 ml)
  2. washwashed with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-1a2e3db287ae4cf68ffdae683a4ebf89
Source dataset
uspto-grants-2016_05
Patent number
US09340556B2

Reaction notes

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