Nitric Acid → 5-Chloro-2-nitrobenzaldehyde

HRID 1649195Notes

Reaction equation

HRID 1649195 reaction equation
[N+:1]([O-:4])(O)=[O:2].S(=O)(=O)(O)O.[Cl:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=1)[CH:14]=[O:15]>C(Cl)Cl>[N+:1]([C:16]1[CH:17]=[CH:18][C:11]([Cl:10])=[CH:12][C:13]=1[CH:14]=[O:15])([O-:4])=[O:2]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 114773-Chlorobenzaldehyde

Product 1

HCID 811235-Chloro-2-nitrobenzaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Concentrated nitric acid (29.3 ml) was added dropwise to 500 ml of concentrated sulfuric acid with ice cooling externally while stirring. In addition, 50 g of m-chlorobenzaldehyde was added dropwise to the resulting mixture at 5° C. or less. After stirring was continued at room temperature for 1 hour the reaction mixture was poured onto ice to precipitate solids which were collected by filtration. After washing with water the solids thus-obtained were dissolved in methylene chloride and the methylene chloride layer was washed with a dilute aqueous sodium hydroxide, washed with water and dried over sodium sulfate. Removal of the solvent by distillation gave 62.3 g of 2-nitro-5-chlorobenzaldehyde, m.p. 65°-69° C.

Workup

  1. stirringAfter stirring
  2. additionthe reaction mixture was poured onto ice
  3. customto precipitate solids which
  4. filtrationwere collected by filtration
  5. washAfter washing with water the solids
  6. customthus-obtained
  7. washthe methylene chloride layer was washed with a dilute aqueous sodium hydroxide
  8. washwashed with water
  9. dry with materialdried over sodium sulfate
  10. customRemoval of the solvent
  11. distillationby distillation

Sources & evidence

ORD record
ord-9a431565718847af81237baecf436953
Source dataset
uspto-grants-1983_11
Patent number
US04415572

Reaction notes

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