Friedel Crafts Acylation - Term Papers - Tlh2588
The Friedel-Crafts Reaction: Acylation of Ferrocene
Toia Hill
August 4, 2011
Organic Chemistry II
Purpose: A Friedel- Crafts acylation is an electrophilic aromatic substitution reaction which introduces an acyl group onto an aromatic ring. The purpose of this lab is to produce acetylferrocene via electrophilic aromatic substitution. Ferrocene was acylated in the more favorable set of detailed methods of phosphoric acid as the catalyst and acetic anhydride.
Reaction
Procedure
Reaction:
1. Add 93 mg of ferrocene to a reaction tube.
2. Using a syringe add 0.35 mL of acetic anhydride.
3. By syringe add 0.1 mL of 85% H3PO4.
4. Cap the reaction tube with a septum and insert a needle.
5. Heat the mixture in boiling water to dissolve Ferrocene.
6. Heat for an additional 10 minutes.
Work up and Purification:
1. Cool the reaction tube in ice water.
2. Dropwise add 0.5 ml of ice water while mixing.
3. Add dropwise 3M of NaOH while mixing, until neutralized to a pH 7.
4. Collect the crude product on Hirsh Funnel and rinse with water.
5. Pull air through the funnel to dry the solid, and finish the drying process by pressing the solid product between two sheets of filter paper
Chromatography
1. Fill the column half full with dry silica gel SiO2.
2. Empty the silica gel into an Erlenmeyer flask, fill it half full with Ligroin, and stir.
3. Swirl these contents in a flask and immediately pour into the column with valve closed.
4. Open the valve and drain some of the solvent back into the flask.
5. Close the valve and continue transferring silica gel SiO2 into the column, and place an empty flask underneath.
6. Drain excess ligroin until a solvent layer of 5mm remains.
7. Tap the column to settle to a minimum height, and pack evenly.
8. With the suction flask dissolve the solid reaction mixture in dichloromethane.
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