Nitric Acid → 2,3-dichloro-6-nitrobenzaldehyde

HRID 41353

Reaction equation

HRID 41353 reaction equation
[Cl:1][C:2]1[C:9]([Cl:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[N+:11]([O-])([OH:13])=[O:12]>S(=O)(=O)(O)O>[Cl:1][C:2]1[C:9]([Cl:10])=[CH:8][CH:7]=[C:6]([N+:11]([O-:13])=[O:12])[C:3]=1[CH:4]=[O:5]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 357452,3-Dichlorobenzaldehyde

Product 1

HCID 112182712,3-dichloro-6-nitrobenzaldehyde

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To 2,3-dichlorobenzaldehyde (20 g, 114 mmol) in concentrated sulfuric acid (100 mL) was added cautiously fuming nitric acid (5.4 mL, 8.16 g, 130 mmol). The resulting solution was stirred for 1 hour, then poured onto an ice/water slurry and the precipitate collected by filtration. This was dissolved in diethyl ether (400 mL), and the solution washed with water and saturated sodium carbonate, then dried (MgSO4) and concentrated. The residue was re-dissolved in the minimum amount of hot diethyl ether, then poured quickly into vigorously stirred petrol (1 L). After stirring for a further 10 minutes, the precipitate was collected by suction filtration and dried under vacuum to yield 2,3-dichloro-6-nitrobenzaldehyde, 9.98 g (40%), essentially free of isomers.

Workup

  1. filtrationthe precipitate collected by filtration
  2. dissolutionThis was dissolved in diethyl ether (400 mL)
  3. washthe solution washed with water and saturated sodium carbonate
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. dissolutionThe residue was re-dissolved in the minimum amount of hot diethyl ether
  7. additionpoured quickly into vigorously stirred petrol (1 L)
  8. stirringAfter stirring for a further 10 minutes
  9. filtrationthe precipitate was collected by suction filtration
  10. customdried under vacuum

Sources & evidence

ORD record
ord-4d805f135fb64ccb8ca0b8cf87bb4f3f
Source dataset
uspto-grants-2013_09
Patent number
US08530651B2

Linked notes

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