Nitric Acid → 4-Isobutyl-3-nitrobenzaldehyde
Reaction equation
[CH2:1]([C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[O:10])=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].S(=O)(=O)(O)O.[N+:18]([O-])([OH:20])=[O:19]>>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([CH:9]=[O:10])=[CH:11][C:12]=1[N+:18]([O-:20])=[O:19])[CH:2]([CH3:4])[CH3:3]Participants
4
Procedure
4-Isobutyl benzaldehyde (7 g, 0.0431 mol) is added drop wise to a mixture of concentrated sulfuric acid & nitric acid (68-72%) (9:1, 60 mL) at 0-5° C. Reaction mixture is allowed to stir at this temperature for 2 hrs, then poured into crushed ice. It is then extracted with ethyl acetate (3×40 mL). Combined organic layer is dried over sodium sulfate and concentrated under reduced pressure. The residue is purified by column chromatography (silica gel, 230-400 mesh, ethyl acetate:n-hexane 1:19) to yield 4-isobutyl-3-nitrobenzaldehyde.