Nitroethane → 2,4-Dichloro-1-(2-nitro-1-propen-1-yl)benzene

HRID 389171Notes

Reaction equation

HRID 389171 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:3]=1[CH:4]=O.C([O-])(=O)C.[NH4+].[N+:16]([CH2:19][CH3:20])([O-:18])=[O:17]>C(OCC)(=O)C>[Cl:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[C:19]([N+:16]([O-:18])=[O:17])[CH3:20]

Participants

5

Reactant 3

HCID 6587NitroethaneHCID 134042,4-DichlorobenzaldehydeHCID 517165Ammonium Acetate

Product 1

HCID 7106762,4-Dichloro-1-(2-nitro-1-propen-1-yl)benzeneYield 52%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2,4-dichlorobenzaldehyde (1.45 g, 8.3 mmol), ammonium acetate (0.64 g, 8.3 mmol) and nitroethane (6 g, 80 mmol) was heated under reflux for 6 hr. The mixture was allowed to cool to room temperature and ethyl acetate was added. The mixture was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated. Recrystallization from ethanol gave 2,4-dichloro-1-(2-nitro-1-propenyl)benzene (yellow needle crystals, yield; 1.0 g, 52%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 6 hr
  3. washThe mixture was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-1399554a04494fd9a666bf997f38615d
Source dataset
uspto-grants-2013_02
Patent number
US08378114B2

Reaction notes

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