Nitric Acid → 4-Butylbenzenesulfonic acid

Reaktionsgleichung

[CH2:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].[S:11](=[O:15])(=[O:14])([OH:13])[OH:12].[N+:16]([O-])([OH:18])=[O:17]>>[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([OH:14])(=[O:13])=[O:12])=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].[N+:16]([C:6]1[CH:7]=[C:8]([S:11]([OH:13])(=[O:15])=[O:12])[CH:9]=[CH:10][C:5]=1[CH2:1][CH2:2][CH2:3][CH3:4])([O-:18])=[O:17]

Komponenten

Edukt 3

HCID 944Nitric Acid

HCID 1118Sulfuric Acid2×

HCID 7705Butylbenzene

Produkt 2

HCID 291174-Butylbenzenesulfonic acid

HCID 202174443-Nitro-4-n-butylbenzenesulfonic acid

Versuchsvorschrift

4-n-butylbenzenesulfonic acid is prepared by sulfonating 4n-butylbenzene with concentrated sulfuric acid at 180° C. as in previous reactions. Nitration of this compound with a mixture of sulfuric acid and nitric acid on a steam bath yielded 3-nitro-4-n-butylbenzenesulfonic acid. Hydrogenation of this in 50% ethanol/water over palladium on charcoal afforded 3-amino-4-n-butylbenzenesulfonic acid. Structural verification was obtained by carbon magnetic resonance, proton magnetic resonance and infra-red analysis.