Nitric Acid → 4-Nitro-2,3,6-trimethylanisole

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Reaction Steps

To a stirred, heated (70°-80° C.) solution of 20.3 g (0.135 mol) of 2,3,6-trimethylanisole in 200 ml of acetic acid was added dropwise 9.65 ml of conc. aqueous HNO3 in 20 ml of acetic acid. After the addition the mixture was poured onto ice, and the resulting mixture was extracted 3 times with methylene chloride. The organic phase was evaporated to remove acetic acid and methylene chloride, and the residue was dissolved in ether and washed twice with NaOH-solution and twice with NaHCO3 -solution. Drying (MgSO4) and evaporation gave 19.0 g (72%) of the product, which was used without further purification in the next step.

Provenance & Evidence