A two step synthesis of methyl 3-nitrobenzene

PROCEDURE

Safety -   Methanol is toxic and extremely flammable

                Conc. Sulphuric acid is corrosive

                Hydrocarbon solvent is flammable

                Methyl benzoate is harmful

STEP 1:  Formation of methyl benzoate from benzoic acid:
  1. Add 8g of benzoic acid, 15cm3 of methanol and 2cm3 of concentrated sulphuric acid to a 50cm3 pear shaped flask.
  2. Add 3-4 anti bumping granules and reflux for 45 minutes.
  3. Cool the mixture to room temperature and pour into a separating funnel that contains 30cm3 of cold water.
  4. Rinse the pear shaped flask with 15cm3 hydrocarbon solvent and pour the washings into the separating funnel.
  5. Shake the flask releasing any gases regularly.
  6. Allow the 2 layers to separate and run off the lower aqueous layer into a conical flask.  (you don't need this solution).
  7. Add 15cm3 of water to your hydrocarbon layer in the separating funnel and shake.
  8. Now add 15cm3 of 0.5M sodium carbonate solution and shake again.
  9. Run off the aqueous layer again into a comical flask.  (you don't need this solution).
  10. Add a small amount of anhydrous sodium sulphate, shake and filter out the sodium sulphate collecting the filtrate in a small round bottom flask.
  11. Remove the hydrocarbon solvent by distilling it off.  Keep distilling and collect the methyl benzoate distillate above 190oC.
  12. Weigh your product.