Nitric Acid → 2-Hydroxy-3-nitrobenzaldehyde

HRID 903106Notes

Reaction equation

HRID 903106 reaction equation
[CH:1](=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[N+:10]([O-])([OH:12])=[O:11]>C(O)(=O)C>[N+:10]([C:5]1[CH:6]=[CH:7][CH:8]=[C:2]([CH:1]=[O:9])[C:3]=1[OH:4])([O-:12])=[O:11]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 6998Salicylaldehyde

Product 1

HCID 789342-Hydroxy-3-nitrobenzaldehyde

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Salicylaldehyde (10 grams) is dissolved in acetic acid (50 grams) and nitrated with 10 ml. of red fuming nitric acid at 40°-45° C. The mixture is poured over ice and filtered. The solid product is a mixture of 3- and 5- nitrosalicylaldehyde. The isomers are separated by fractional recrystallization in acetic acid or by fractional recrystallization of their sodium salts in warm water, the 5-nitro isomer being less soluble in water than the 3-nitro isomer.

Workup

  1. customat 40°-45° C
  2. additionThe mixture is poured over ice
  3. filtrationfiltered
  4. additiona mixture of 3- and 5- nitrosalicylaldehyde
  5. customThe isomers are separated by fractional recrystallization in acetic acid or by fractional recrystallization of their sodium salts in warm water

Sources & evidence

ORD record
ord-8a772cd0d78645dfafb8e42763e3ec8a
Source dataset
uspto-grants-1980_10
Patent number
US04226792

Reaction notes

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