Synthesis of 5,5-Diphenyl-4-penten-2-one: A Variation on a Classic Organic Synthesis Laboratory

Author:

Alber Joshua P.1,DeGrand Michael J.1,Cermak Diana M.1

Affiliation:

1. Department of Chemistry, Knox College, Galesburg, Illinois 61401, United States

Publisher

American Chemical Society (ACS)

Subject

Education,General Chemistry

Reference9 articles.

1. The ethylene ketal protecting group in organic synthesis. An undergraduate laboratory experiment

2. Preparation of 1,1-Diphenyl-1-hydroxy-3-butanone

3. The Ethylene Ketal Protecting Group Revisited: The Synthesis of 4-Hydroxy-4,4-diphenyl-2-butanone

4. Harwood, L. M.; Moody, C. J.Experimental Organic Chemistry: Principles and Practice,1st dd.Blackwell Scientific Publications:Boston, 1989; pp540−542.

5. We have followed several Grignard experiments for workup of the Grignard product. We have tried using water (Paulson et. al., Harwood and Moody); aqueous HCl solution (Weiss, H. M.J. Chem. Educ.1999,76, 76−77); and aqueous H2SO4solutions (Organic Syntheses;Wiley & Sons:New York, 1941; Collect. Vol.I, pp188−190.Furniss, B. S.; Hannaford, A. J.; Smith, P. W. G.; Tatchell, A. R.Vogel’s Practical Organic Chemistry,5th ed.Longman Scientific & Technical:New York, 1989; pp534−541). We have found that use of H2SO4solutions work best to dissolve the Mg salts that form upon the quench and make extraction much more efficient.

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