Nitric Acid → 2-Hydroxy-5-methoxy-3-nitrobenzaldehyde

HRID 466264

Reaktionsgleichung

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

Komponenten

Reaktionsbedingungen

Temperatur: 15 °C

Versuchsvorschrift

First, 8.0 g (52.6 mmol) of 5-methoxysalicylaldehyde 5 was dissolved in 50 ml of acetic acid. Then, a mixed solution of 2.5 ml (59.7 mmol) of fuming nitric acid (99%, specific gravity 1.52) and 8 ml of acetic acid was added dropwise into the above mixture over a period of 1 hour while maintaining the temperature of the reaction mixture at approximately 15° C. with ice-cold water and strongly agitating the reaction mixture. Agitation was further continued for 7 hours. The precipitate formed was filtered, after which the precipitate was recrystallized from 500 ml of ethanol, thereby obtaining 4.2 g (21.3 mmol, yield 40.5%) of 3-nitro-5-methoxysalicylaldehyde 6 in the form of yellow needle crystals. This reaction can be expressed by the following chemical equation: ##STR7##

Aufarbeitung

customThe precipitate formed
filtrationwas filtered
customafter which the precipitate was recrystallized from 500 ml of ethanol

Quellen und Nachweise

ORD-Eintrag: ord-2052b12a97224c04ae489bf0ceb1aef4
Quelldatensatz: uspto-grants-1992_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05155230

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