Nitric Acid → 4-Hydroxy-2,5-dimethyl-3-nitrobenzaldehyde

HRID 1271202Notes

Reaction equation

HRID 1271202 reaction equation
[Cl-].[Na+].[OH:3][C:4]1[C:11]([CH3:12])=[CH:10][C:7]([CH:8]=[O:9])=[C:6]([CH3:13])[CH:5]=1.[N+:14]([O-])([OH:16])=[O:15]>S(=O)(=O)(O)O>[OH:3][C:4]1[C:11]([CH3:12])=[CH:10][C:7]([CH:8]=[O:9])=[C:6]([CH3:13])[C:5]=1[N+:14]([O-:16])=[O:15]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 5234Sodium ChlorideHCID 128272904-Hydroxy-2,5-dimethyl-benzaldehyde

Product 1

HCID 184523704-Hydroxy-2,5-dimethyl-3-nitrobenzaldehyde

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

To a −10° C. (ice and sodium chloride) solution of 4-hydroxy-2,5-dimethylbenzaldehyde (1.0 g, 6.65 mmol) in concentrated sulfuric acid (10 mL) was added dropwise 70% (concentrated) nitric acid (0.598 g, 6.65 mmol) in 2 mL concentrated sulfuric acid. The reaction stirred for approximately 30 minutes. The reaction was then poured onto crushed ice. The precipitate was collected and washed with water. The solid was then dried on a high vacuum pump to yield a white solid. Microanalysis (C9H9N1O4): calculated: C=55.39, H=4.65, N=7.18; found: C=55.60, H=4.65, N=7.02. MS: M+−1=194.1 Da.

Workup

  1. additionThe reaction was then poured
  2. customonto crushed ice
  3. customThe precipitate was collected
  4. washwashed with water
  5. customThe solid was then dried on a high vacuum pump
  6. customto yield a white solid

Sources & evidence

ORD record
ord-9b5335326da04d57887a62fa2e30869b
Source dataset
uspto-grants-2007_04
Patent number
US07205295B2

Reaction notes

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