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

HRID 481138

Reaction equation

HRID 481138 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].CC(CC(C1C(O)=CC(O)=C(CC=C(C)C)C=1[O-])=O)C.ClC1C(Cl)=CC([N+]([O-])=O)=CC=1C=O>S(=O)(=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

7

Reactant 4

HCID 944Nitric AcidHCID 357452,3-Dichlorobenzaldehyde2×HCID 187671622,3-Dichloro-5-nitrobenzaldehydeHCID 252006104-Prenylphlorisovalerophenone

Product 1

HCID 112182712,3-Dichloro-6-nitrobenzaldehyde

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Conditions

Temperature
22.5 °C

Procedure

A solution of 40 g of 2,3-dichlorobenzaldehyde (compound IX) in 160 mL of concentrated sulfuric acid (95-98% w/w) is heated to 40° C. and stirred to form a solution, then cooled to 20-25° C. Concentrated nitric acid (69-71% w/w; 24.7 g) is added to this solution over 20 minutes (an ice bath is used to maintain a reaction temperature of 20-30° C.). The reaction mixture is stirred at room temperature for 1 hour, and then added in portions to 600 mL of water. The resulting suspension is stirred for 2 hours and filtered. The filter cake is washed (3×50 mL of water). The filter cake is agitated with 200 mL of water for 2 hours and filtered. The filter cake is washed (3×50 mL of water) and dried in vacuo to give a mixture of the compound X and the isomer, 2,3-dichloro-5-nitrobenzaldehyde.

Workup

  1. customto form a solution
  2. temperatureto maintain a reaction temperature of 20-30° C.)
  3. stirringThe reaction mixture is stirred at room temperature for 1 hour
  4. stirringThe resulting suspension is stirred for 2 hours
  5. filtrationfiltered
  6. washThe filter cake is washed (3×50 mL of water)
  7. stirringThe filter cake is agitated with 200 mL of water for 2 hours
  8. filtrationfiltered
  9. washThe filter cake is washed (3×50 mL of water)
  10. customdried in vacuo
  11. customto give

Sources & evidence

ORD record
ord-229204585ba346d59904f042af95521b
Source dataset
uspto-grants-2003_11
Patent number
US06653500B2

Linked notes

Loading…