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

HRID 2274736Notes

Reaction equation

HRID 2274736 reaction equation
C(O)(=O)C.[C:5]([OH:16])(=[O:15])[C:6]1[CH:14]=[CH:13][C:11]([OH:12])=[C:8]([O:9][CH3:10])[CH:7]=1.[N+:17]([O-])([OH:19])=[O:18]>O>[OH:12][C:11]1[C:8]([O:9][CH3:10])=[CH:7][C:6]([C:5]([OH:16])=[O:15])=[CH:14][C:13]=1[N+:17]([O-:19])=[O:18]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 944Nitric AcidHCID 8468Vanillic Acid

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A reactor was charged with 525 kg of glacial acetic acid and 50 kg vanillic acid. The mixture was heated with warm water gradually to 50° C. in around 75 minutes. Temperature was set to 16° C. Nitric acid, 31.4 kg was then added gradually over a period of 3 hrs. When the administration was complete the mixture was allowed to stir for additional 3.5-4.5 hours.

Workup

  1. customwas set to 16° C

Sources & evidence

ORD record
ord-508357ccb6cb4bd7b7e78ebceb42009a
Source dataset
uspto-grants-2015_09
Patent number
US09126988B2

Reaction notes

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