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

HRID 2274738Notes

Reaction equation

HRID 2274738 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 AcidHCID 8468Vanillic Acid

Product 1

HCID 155279394-Hydroxy-3-methoxy-5-nitrobenzoic acidYield 40%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The process of Example 1a was scaled up to employ vanillic acid (375 g) in acetic acid (3940 g) to which was added nitric acid (65%, 245 g) at 12° C. over 3 hours followed by stirring for one hour. The overall yield was 40% of a 99.9% pure product.

Sources & evidence

ORD record
ord-b1952745399d466ca3a3d2d2fc814c7b
Source dataset
uspto-grants-2015_09
Patent number
US09126988B2

Reaction notes

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