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

HRID 329243Notes

Reaction equation

HRID 329243 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:3]=1[CH:4]=O.[N+:11]([CH2:14][CH3:15])([O-:13])=[O:12].C([O-])(=O)C>C(O)(=O)C>[Cl:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[C:14]([N+:11]([O-:13])=[O:12])[CH3:15]

Participants

5

Reactant 3

HCID 175AcetateHCID 6587NitroethaneHCID 134042,4-Dichlorobenzaldehyde

Product 1

HCID 7106762,4-Dichloro-1-(2-nitro-1-propen-1-yl)benzeneYield 60%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The 1-aryl-2-nitropropenes were prepared according to the procedure of Koremura, Oku, Shono and Nakanishi (6). The starting aldehydes, commercially available, were used without further purification. To prepare 1-(2,4-dichlorophenyl)-2-nitropropene, a mixture of 43.5 g (0.25 mol) of 2,4-dichlorobenzaldehyde, 18.75 g (0.25 mol) of 1-nitroethane, and 20 g of ammmonium acetate, dissolved in 100 ml of glacial acetic acid, was refluxed for two hours, and then poured onto 200 g of ice. The yellow precipitate was collected and recrystallized from absolute ethanol to give 32 g (60%) of 1-(2,4-dichlorophenyl)-2-nitropropene mp 75°; ir (KBr) 1661 (C=C), 1520 and 1319 cm-1 (NO2).

Workup

  1. customThe starting aldehydes, commercially available, were used without further purification
  2. customTo prepare 1-(2,4-dichlorophenyl)-2-nitropropene
  3. temperaturewas refluxed for two hours
  4. customThe yellow precipitate was collected
  5. customrecrystallized from absolute ethanol

Sources & evidence

ORD record
ord-da580f40e3384030877902286cdfcb0a
Source dataset
uspto-grants-1977_04
Patent number
US04020111

Reaction notes

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