Potassium Nitrate → 2,3-Dichloro-6-nitrobenzaldehyde

HRID 731676

Reaction equation

HRID 731676 reaction equation
[N+:1]([O-:4])([O-])=[O:2].[K+].[Cl:6][C:7]1[C:14]([Cl:15])=[CH:13][CH:12]=[CH:11][C:8]=1[CH:9]=[O:10]>S(=O)(=O)(O)O>[Cl:6][C:7]1[C:14]([Cl:15])=[CH:13][CH:12]=[C:11]([N+:1]([O-:4])=[O:2])[C:8]=1[CH:9]=[O:10]

Participants

4

Reactant 2

HCID 24434Potassium NitrateHCID 357452,3-Dichlorobenzaldehyde

Product 1

HCID 112182712,3-Dichloro-6-nitrobenzaldehydeYield 34.5%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Potassium nitrate (578 mg, 5.71 mmol) was dissolved in concentrated sulfuric acid (4.5 mL) and added dropwise to a stirred solution of 2,3-dichlorobenzaldehyde (1.0 g, 5.71 mmol) at room temperature. The mixture was left without stirring for 10 days at room temperature. Material that had crystallized out of the reaction mixture was collected by filtration to afford 2,3-dichloro-6-nitrobenzaldehyde (196MBT36, 433 mg, 34%) as yellow needles. Regioselectivity was confirmed by the Bayer-Drewson indigo synthesis.

Workup

  1. waitThe mixture was left
  2. customMaterial that had crystallized out of the reaction mixture
  3. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-5e952184a2824600b6a45a378c0af399
Source dataset
uspto-grants-2009_09
Patent number
US07585877B2

Linked notes

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