Nitric Acid → HCID 66889382, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 90% nitric acid (40 mL) and concentrated sulfuric acid (8 mL) were cooled to −5° C. followed by portionwise addition of solid methyl 3-(acetyloxy)-4-(methyloxy)benzoate (25.9 g, 115 mmol.) over 25 minutes. After stirring for 5 minutes the solution was poured onto ice and the aqueous mixture was extracted once with dichloromethane. The organic solution was then washed with dilute aqueous sodium hydrogencarbonate (3×) then once with water and dried over anhydrous magnesium sulfate. Filtration and concentration followed by suspension of the solid residue in hexanes and filtration gave methyl 3-(acetyloxy)-4-(methyloxy)-5-nitrobenzoate (27.2 g, 88% yield) as a white solid on drying. 1H NMR (400 MHz, CDCl3): 8.38 (d, 1H), 7.99 (d, 1H), 4.00 (s, 3H), 3.95 (s, 3H), 2.40 (s, 3H).

Provenance & Evidence