Nitric Acid → Methyl 4-(3-methoxy-3-oxopropyl)-3-nitrobenzoate

Participants

Reaction Steps

To a mixture of methyl 4-(3-methoxy-3-oxopropyl)benzoate (10 g) and sulfuric acid (50 ml) was added dropwise fumed nitric acid (5.7 ml) under ice-cooling, followed by stirring at room temperature for 4 hours. The reaction mixture was poured into ice-water and extracted with chloroform. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. To the residue were added methanol and concentrated sulfuric acid, followed by stirring at 105° C. for 1 hour. The reaction mixture was concentrated under reduced pressure, and a saturated aqueous sodium hydrogen carbonate solution was added to the residue under ice-cooling. The resulting solid was collected by filtration and washed with a saturated aqueous sodium hydrogen carbonate solution and water to obtain methyl 4-(3-methoxy-3-oxopropyl)-3-nitrobenzoate (12 g).

Provenance & Evidence