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Ferrocene and its derivatives have numerous applications to polymers with semiconductor properties, pharmaceuticals and fine chemicals. The organometallic compound has a unique sandwich structure resulting in interesting physical and chemical properties. Acetylferrocene is one of the more common acyl derivatives of ferrocene and is easily prepared by the classical Friedel-Crafts reaction under mild conditions in the presence of a Lewis acid catalyst such as phosphoric acid and acetic anhydride.
The molecule is air-stable and soluble in most organic solvents. The acetyl group has a lower melting point than the parent molecule, ferrocene. This is because the acetyl group adds a polar oxygen to the ring system, decreasing its molecular symmetry. In addition, acetyl ferrocene is highly reactive and has low electronegativity.
The traditional Friedel-Crafts acylation reaction has many drawbacks including byproduct formation, release of toxic volatile organic solvents into the atmosphere and corrosion issues . A more environmentally benign approach is to use ionic liquids (ILs) as the reaction solvent. ILs are solely composed of (organic) cations and (organic/inorganic) anions and have very low vapor pressure, low flammability and high solvency power.
To prepare acetylferrocene, combine 0.4 g of ferrocene with 2 mL of acetic anhydride and 0.5 mL of 85% phosphoric acid in a test tube. Stir the mixture and heat it in a water bath at 60 to 80 oC for 5 minutes. The solution is then cooled to room temperature and transferred into a clean flask. Check the reaction by TLC using 4:1 petroeum ether / MTBE and you should observe an orange spot for the product and yellow spots for the starting material. Combine in a tared flask the fractions that contain the pure product and evaporate the solvent, then record the weight of the acetylferrocene produced.