Methyl Benzoate
In this experiment, we used methyl benzoate from the last experiment with HNO3 and H2SO4 to synthesize methyl 3-nitrobenzoate. First we added methyl benzoate to 12 mL cooled conc. Sulfuric acid in a flask. In a separate flask, we made a solution of 4 mL conc. Sulfuric acid and 4 mL nitric acid and then added dropwise to the solution of methyl benzoate in an ice bath on a stir plate while maintaining the temperature of reaction between 5-15 °C. After the addition was complete we took the flask out of the ice bath and placed it back on the stir plate for about 20 minutes to complete the reaction. Then we poured the mixture in the beaker filled with ice and white solid started to precipitate out. After all the ice melted we used suction filtration
to collect the crude product. We washed the crude product with water and two portions of 10 mL ice cold methanol. The we weighed the crude product in tared flask and added the equal amount of methanol for recrystallization. We dissolved the crude product in methanol on a hot plate. Then we allowed the solution to cool at room temperature and then in ice so the product started recrystallizing. We used suction filtration to collect final product and left it on the funnel to dry. H-NMR was obtained for product analysis. The spectrum shows three peaks between 7-9 ppm which are all from the benzene ring. The downfield peak at 8.9 ppm is from the H between the nitro and methyl ester group. The overlapped peaks at 8.4 ppm are from the two hydrogens that are beside the electron withdrawing groups and the peak at 7.7 ppm is from the hydrogen that is farthest away from the electron withdrawing groups. The peak at 4.0 ppm is from the methyl group hydrogens that is attached to the oxygen from ester. We calculated actual yield of the final product which was 5.529 g and percent yield which was 67.82%. The final product was solid white compound in color/appearance.
to collect the crude product. We washed the crude product with water and two portions of 10 mL ice cold methanol. The we weighed the crude product in tared flask and added the equal amount of methanol for recrystallization. We dissolved the crude product in methanol on a hot plate. Then we allowed the solution to cool at room temperature and then in ice so the product started recrystallizing. We used suction filtration to collect final product and left it on the funnel to dry. H-NMR was obtained for product analysis. The spectrum shows three peaks between 7-9 ppm which are all from the benzene ring. The downfield peak at 8.9 ppm is from the H between the nitro and methyl ester group. The overlapped peaks at 8.4 ppm are from the two hydrogens that are beside the electron withdrawing groups and the peak at 7.7 ppm is from the hydrogen that is farthest away from the electron withdrawing groups. The peak at 4.0 ppm is from the methyl group hydrogens that is attached to the oxygen from ester. We calculated actual yield of the final product which was 5.529 g and percent yield which was 67.82%. The final product was solid white compound in color/appearance.