Nitric Acid → 2,4-Dichloro-5-nitrobenzaldehyde

HRID 566609Notes

Reaction equation

HRID 566609 reaction equation
[N+:1]([O-:4])(O)=[O:2].[Cl:5][C:6]1[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:7]=1[CH:8]=[O:9]>S(=O)(=O)(O)O>[Cl:5][C:6]1[CH:13]=[C:12]([Cl:14])[C:11]([N+:1]([O-:4])=[O:2])=[CH:10][C:7]=1[CH:8]=[O:9]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 134042,4-Dichlorobenzaldehyde

Product 1

HCID 33036592,4-Dichloro-5-nitrobenzaldehyde

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
10 °C

Procedure

A solution of 125 g of nitric acid in 153 g of sulfuric acid which had been prepared with ice-cooling at (−5)° C. was added dropwise to a solution of 262.5 g (1.5 mol) of 2,4-dichlorobenzaldehyde in 560 ml of sulfuric acid. After the reaction mixture had been stirred for 2 hours at 10° C., it was poured onto 4 kg of ice. The resulting solids were subsequently separated off, washed with water and dissolved in 2 l of dichloromethane. The resulting solution was washed with saturated aqueous sodium hydrogen carbonate solution, then dried over magnesium sulfate and finally concentrated. Yield: 329.5 g; m.p.: 61-63° C.

Workup

  1. temperaturecooling at (−5)° C
  2. customThe resulting solids were subsequently separated off
  3. washwashed with water
  4. dissolutiondissolved in 2 l of dichloromethane
  5. washThe resulting solution was washed with saturated aqueous sodium hydrogen carbonate solution
  6. dry with materialdried over magnesium sulfate
  7. concentrationfinally concentrated

Sources & evidence

ORD record
ord-8fff591a5bf74429abe560bda9c69a2a
Source dataset
uspto-grants-2001_01
Patent number
US06175007B1

Reaction notes

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