Methyl p-nitrophenylacetate

Synthesis

4-nitrophenylacetic acid(2.00 g, 11 mmol) was added to a clean carousel tube. Dimethyl carbonate (3 mL, 3.21 g, 35.6 mmol) was added, and the reaction was heated at reflux overnight. The brown solution was allowed to cool, and poured in to aqueous sodium bicarbonate (10%, 10 mL) while stirring. The resulting mixture was extracted with ethyl acetate (3 x 10 mL). The combined organic layers were washed with water and brine (10 mL each), and dried over anhydrous magnesium sulphate. After filtration and evaporation of the solvents, proton NMR analysis showed the product had formed, and none of the precursor acid remained. No further purification was performed. This gave methyl p-nitrophenylacetate as a pale orange oil (1.929 g, 9.89 mmol, 90%)): 1H NMR (400 MHz, CDCl 3 ) |? 8.20 (d, J = 8.6 Hz, 2H), 7.46 (d, J = 8.6 Hz, 2H, 3.74 (s, 2H), 3.73 (s, 3H).