Chemistry 351 Laboratory - Spring Semester 2011

Expt #5. A New Method for Friedel-Crafts Acylation: Acetylation of Anisole.

Relevant textbook readings - Smith, Chapter 18

Reference for Procedure - Sarvari, M. H.; Sharghi, H. J. Org. Chem., 2004, 69, 6953–6956

Overview - You will acetylate anisole using the procedure outlined in the experimental part of the above Journal of Organic Chemistry reference. The reactants and product are shown in Entry 10, Table 1.

Procedure Notes

1. Run the reaction at five times the scale of the literature procedure. You decide what glassware to use.
2. Evaporation of the solvent will be carried out using the rotary evaporator.
3. Determine the yield of crude product.
4. Save a sample of the crude product for mp determination. Recrystallize the rest using ethanol as solvent.
5. Obtain the mp as well as ¹H  NMR and IR spectra of the final crystalline product.