Nitration of Methyl Benzoate

O O CH3 H2SO 4 O CH3

HONO 2

+
N O O methyl 3-nitrobenzoate

H2O

methyl benzoate

Procedure
Dispense 6.0 mL of concentrated sulfuric acid in a 150 mL beaker. Place in a salt ice bath for 15 minutes. At the same time add 2.0 mL of concentrated sulfuric acid and 2.0 mL of concentrated nitric acd in a 50 mL beaker. Place this 50 mL beaker in a salt ice bath for 15 minutes. Dispense 2.8 mL of methylbenzoate in a different 50 mL beaker. After the 15 minutes of the 6.0 mL concentrated sulfuric acid being in a ice bath, slowly add the 2.8 mL of methylbenzoate using a Pasteur pipette to the150 mL beaker. Then slowly add the 50/50 ratio of the concentrated acid to the 150 mL beaker. Constantly mix the reaction mixture with a glass stirring rod during the addition of the concentrated acids. This addition of the concentrated acids should take 5 minutes. Then remove the 150 mL reaction beaker from the ice bath and place on the counter for 15 minutes.

In a 150 mL beaker weigh out 25 grams of ice, pour the reaction mixture in the 150 mL beaker in the 150 mL beaker with ice. Stir for two minutes with glass stirring rod. Then vacuum filtrate the precipitate. Each rinse first pour into the reaction beaker to help transfer all the product to the vacuum apparatus. First rinse is 12 mL ice D.I. cold water Second rinse is 12 mL ice cold D.I. water Third rinse is 5 mL ice cold methanol Fourth rinse is 5 mL ice cold methanol Note : start cooling the 24 mL of D.I. water and 10 mL methanol at the beginning of the lab. Crystallize in methanol, vacuum filtrate, allow to air dry for 30 minutes. Weigh the product, calculate percent yield and obtain an IR.

Conclusion
percent yield and compare IRs.