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  Home > JCE Print > Journal of Chemical Education > Issues > 2002  > January  >
In the Laboratory
The Microscale Laboratory
Wittig Reaction: The Synthesis of trans-9-(2-Phenylethenyl)anthracene Revisited
Christine Jaworek and Sarah Iacobucci
Department of Chemistry, Tufts University, Medford, MA 02155
Cover
January 2002
Vol. 79 No. 1
p. 111
Abstract
The revisit to this experimental procedure resulted in making a good undergraduate laboratory procedure even better. In this Wittig reaction, readily available starting materials are used; only the trans isomer is produced; the clear and characteristic 1H NMR spectrum of the product is ideal for a lesson in coupling constants to determine stereochemistry; and the product can be readily used in additional brilliant chemiluminescence laboratory experiments. The problematic step of generating tough emulsions during extractions with halogenated solvents has been eliminated by using N,N-dimethylformamide as the reaction solvent and readily precipitating the product from the reaction mixture using 1-propanol and water.
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NMR data are available.
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*  Citation
 Jaworek, Christine; Iacobucci, Sarah. J. Chem. Educ. 2002 79 111.
*  Keywords
 Chromatography; Laboratory Instruction; Luminescence; Microscale; Organic Chemistry; Organic Synthesis
*  History
 Created:
Last Updated:		 December 3, 2001
March 16, 2005
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