Acetic Acid → 1-(2',3'-Dichlorophenyl)-2-nitroethylene

HRID 1789226Notes

Reaction equation

HRID 1789226 reaction equation
[Cl:1][C:2]1[C:9]([Cl:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.C([O-])(=O)C.[NH4+].[N+:16]([CH3:19])([O-:18])=[O:17].C(O)(=O)C>C(Cl)(Cl)Cl>[Cl:1][C:2]1[C:9]([Cl:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[CH:19][N+:16]([O-:18])=[O:17]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6375NitromethaneHCID 357452,3-DichlorobenzaldehydeHCID 517165Ammonium Acetate

Product 1

HCID 35036541-(2',3'-Dichlorophenyl)-2-nitroethylene

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

28.0 g of 2,3-dichlorobenzaldehyde, 13.9 g of ammonium acetate, 13.9 ml of nitromethane and 120 ml of glacial acetic acid are refluxed for 2 hours. After cooling, the reaction mixture is poured onto ice and stirred for 30 minutes. The formed precipitate is then filtered off, washed with water and dried in vacuo to thus obtain the product in the form of slightly yellowish crystals, m.p. 89°-91° C. IR (CHCl3) in cm-1 : 1650 (C=C); 1530 and 1350 (NO2). NMR (CDCl3) in ppm: 7.2-7.7 (m, 4H); 8.50 (d, J=15 Hz, 1H).

Workup

  1. temperatureAfter cooling
  2. additionthe reaction mixture is poured onto ice
  3. filtrationThe formed precipitate is then filtered off
  4. washwashed with water
  5. customdried in vacuo
  6. customto thus obtain the product in the form of slightly yellowish crystals, m.p. 89°-91° C

Sources & evidence

ORD record
ord-230c462de1a74c1688f3fcda4928a955
Source dataset
uspto-grants-1987_08
Patent number
US04687861

Reaction notes

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