Nitric Acid → 2-Nitro-4-chloro-6-methylanisole

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Reaction Steps

4-Chloro-2-methylanisole (46.8 g) was added dropwise to a mixture of concentrated HNO3 (33 ml) and H2SO4 (99 ml) at 0° C. The reaction mixture was then poured into a ice water and extracted with dichloromethane. The organic layer was washed with water, dried over MgSO4, and concentrated in vacuo to give a residue. The residue was purified by flash chromatography over silica gel (elution with 5% ethyl acetate in hexanes) to give 25 g (41%) of 2-nitro-4-chloro-6-methylanisole. 1H NMR (300 MHz, CDCl3) δ7.64 (d, J=2.5 Hz, 1 H), 7.40 (d, J=2.5 Hz, 1 H), 3.89 (s, 3 H), 2.36 (s, 3 H).

Provenance & Evidence