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

Participants

Reaction Conditions

Reaction Steps

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##

Provenance & Evidence