Nitric Acid → 4-Hydroxy-3-methoxy-5-nitrobenzoic acid

HRID 2274737Notes

Reaction equation

HRID 2274737 reaction equation
[C:1]([OH:12])(=[O:11])[C:2]1[CH:10]=[CH:9][C:7]([OH:8])=[C:4]([O:5][CH3:6])[CH:3]=1.[N+:13]([O-])([OH:15])=[O:14]>C(O)(=O)C>[OH:8][C:7]1[C:4]([O:5][CH3:6])=[CH:3][C:2]([C:1]([OH:12])=[O:11])=[CH:10][C:9]=1[N+:13]([O-:15])=[O:14]

Participants

4

Reactant 2

HCID 944Nitric Acid2×HCID 8468Vanillic Acid

Product 1

HCID 155279394-Hydroxy-3-methoxy-5-nitrobenzoic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A suspension of vanillic acid (68.8 kg) in acetic acid (720 kg) is cooled to 17° C. before an excess of a 65% nitric acid (44.0 kg) is added. After complete dosage of nitric acid the suspension is stirred for 2 hours. The suspension is filtered off and the wet cake is successively washed with acetic acid (80.0 kg), acetic acid/water (1:2 w/w—105 kg) and finally water (80 kg—if necessary repeat). The solid is dried at 52° C. for NMT 12 hours prior going to next step.

Workup

  1. additionis added
  2. filtrationThe suspension is filtered off
  3. washthe wet cake is successively washed with acetic acid (80.0 kg), acetic acid/water (1:2 w/w—105 kg) and finally water (80 kg—if necessary repeat)
  4. customThe solid is dried at 52° C. for NMT 12 hours

Sources & evidence

ORD record
ord-b1de8e06c0d6402c99ae24a6ff280740
Source dataset
uspto-grants-2015_09
Patent number
US09126988B2

Reaction notes

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