Benzoic Acid → 3-Nitro-5-sulfobenzoic acid

HRID 235787

Reaction equation

HRID 235787 reaction equation
C(O)(=O)C1C=CC=CC=1.S(=O)(=O)(O)O.S(=O)(=O)=O.[S:19]([C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=1)[C:26]([OH:28])=[O:27])([OH:22])(=[O:21])=[O:20].[N+:32]([O-])([OH:34])=[O:33]>>[N+:32]([C:30]1[CH:29]=[C:25]([CH:24]=[C:23]([S:19]([OH:22])(=[O:21])=[O:20])[CH:31]=1)[C:26]([OH:28])=[O:27])([O-:34])=[O:33]

Participants

6

Reactant 5

HCID 243Benzoic AcidHCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 8477Benzoic acid, 3-sulfo-HCID 24682Sulfur trioxide

Product 1

HCID 27491853-Nitro-5-sulfobenzoic acid

Procedure

Benzoic acid was sulfonated by heating it with concentrated sulfuric acid in the presence of sulfur trioxide. The 3-sulfobenzoic acid was nitrated with fuming nitric acid to yield 3-nitro-5-sulfobenzoic acid. Hydrogenation of this in 50% ethanol/water over palladium on charcoal easily afforded 3-amino-5-sulfobenzoic acid in good yield. Structural verification was obtained by carbon magnetic resonance, proton magnetic resonance and infra-red analysis.

Sources & evidence

ORD record
ord-747374bb87c74b8c8c7bfdc4ca2aba2a
Source dataset
uspto-grants-1987_02
Patent number
US04642240

Linked notes

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