Unit A23 4.10 Aromatic chemistry

Question 1

4.10.5 - Preparation of methyl 3-nitrobenzoate

Answer 1

• Dissolve some of methyl benzoate in some concentrated sulfuric acid.
• Cool the solution in ice.
• Prepare the nitrating mixture by carefully adding concentrated sulfuric acid to concentrated nitric acid and then cool this mixture in ice.
• Add the nitrating mixture drop by drop to the solution of the methylbenzoate, stirring with a thermometer and keeping the temperature below 10 °C.
• When the addition is complete allow the mixture to stand at room temperature for 15 minutes.
• Pour the reaction mixture onto crushed ice and stir until all the ice has melted and crystalline methyl 3-nitrobenzoate is formed.
• Filter the crystals using Buchner filtration, wash with cold water, recrystallise from ethanol, filter off and dry.