Acetic Acid → 3,4-Dihydroxy-5-nitrobenzaldehyde

HRID 1088891Notes

Reaction equation

HRID 1088891 reaction equation
[N+:1]([C:4]1[C:5]([OH:14])=[C:6]([O:12]C)[CH:7]=[C:8]([CH:11]=1)[CH:9]=[O:10])([O-:3])=[O:2].C(O)(=O)C.C>Br>[OH:12][C:6]1[CH:7]=[C:8]([CH:11]=[C:4]([N+:1]([O-:3])=[O:2])[C:5]=1[OH:14])[CH:9]=[O:10]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 297MethaneHCID 811345-Nitrovanillin

Product 1

HCID 57489573,4-Dihydroxy-5-nitrobenzaldehyde

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Conditions

Temperature
-10 °C

Procedure

A solution containing 8.0 kg of 5-nitrovanillin and 8.7 kg of acetic acid in 35 kg of conc. hydrobromic acid was refluxed for 20 h. 0.6 kg of charcoal was added and the mixture was filtered. 32 kg of water was added with stirring and the solution was cooled to -10° C. and stirring was continued for 2 h more. The crystalline product was filtered and washed with water. Yield 5.66 kg (80%), m.p. 135°-137° C.

Workup

  1. temperaturewas refluxed for 20 h
  2. filtrationthe mixture was filtered
  3. addition32 kg of water was added
  4. stirringstirring
  5. filtrationThe crystalline product was filtered
  6. washwashed with water

Sources & evidence

ORD record
ord-7ce3bc4e06c44d1d9509ca84b3ffb8fd
Source dataset
uspto-grants-1990_10
Patent number
US04963590

Reaction notes

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