Nitric Acid → 2,3-Dichloro-6-nitrobenzaldehyde

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Reaction Steps

To 2,3-dichlorobenzaldehyde (20 g, 114 mmol) in concentrated sulfuric acid (100 mL) was added cautiously fuming nitric acid (5.4 mL, 8.16 g, 130 mmol). The resulting solution was stirred for 1 hour, then poured onto an ice/water slurry and the precipitate collected by filtration. This was dissolved in diethyl ether (400 mL), and the solution washed with water and saturated sodium carbonate, then dried (MgSO4) and concentrated. The residue was re-dissolved in the minimum amount of hot diethyl ether, then poured quickly into vigorously stirred petrol (1 L). After stirring for a further 10 minutes, the precipitate was collected by suction filtration and dried under vacuum to yield 2,3-dichloro-6-nitrobenzaldehyde, 9.98 g (40%), essentially free of isomers.

Provenance & Evidence