Nitric Acid → 2-Hydroxy-3-nitrobenzaldehyde

HRID 1487210Notes

Reaction equation

HRID 1487210 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[N+:10]([O-])([OH:12])=[O:11].O>C(O)(=O)C>[OH:1][C:2]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 962WaterHCID 6998Salicylaldehyde

Product 1

HCID 789342-Hydroxy-3-nitrobenzaldehydeYield 26.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 2-hydroxybenzaldehyde (5.0 g, 41 mmol) in acetic acid (50 mL) at 0° C. was added nitric acid (65%, 4 g) dropwise. The reaction mixture was slowly warmed to room temperature for 2 hours and then heated at 40° C. for another 5 hours. The resulting mixture was poured into ice (75 g) and water (500 g). The precipitates were filtrated and purified by silica gel chromatography to afford the product 2-hydroxy-3-nitrobenzaldehyde (1.8 g, yield 26%). 1H NMR (400 MHz, CDCl3) δ ppm 11.44 (s, 1H), 10.42 (s, 1H), 8.34-8.37 (dd, 1H, J=2.0 Hz, 8.4 Hz), 8.10-8.13 (dd, 1H, J=2.0 Hz, 7.6 Hz), 7.12-7.16 (t, 1H, J=8.0 Hz).

Workup

  1. temperatureheated at 40° C. for another 5 hours
  2. filtrationThe precipitates were filtrated
  3. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-62657ff811e6440ba365cfbd4e8504af
Source dataset
uspto-grants-2016_08
Patent number
US09428508B2

Reaction notes

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