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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 38, 2008 - Issue 22
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Original Articles

Procedure for the Rapid Synthesis of the Monomer 1,4-Bis(chloromethyl)-2-(2-ethylhexyloxy)-5-methoxybenzene

Nichole Anderson Chemistry and Materials Division, Michelson Laboratory, Naval Air Warfare Center, China Lake, California, USA
,
Whitney Bagge Chemistry and Materials Division, Michelson Laboratory, Naval Air Warfare Center, China Lake, California, USA
,
Cindy Webber Chemistry and Materials Division, Michelson Laboratory, Naval Air Warfare Center, China Lake, California, USA
,
Peter Zarras Chemistry and Materials Division, Michelson Laboratory, Naval Air Warfare Center, China Lake, California, USA
&
Matthew C. Davis Chemistry and Materials Division, Michelson Laboratory, Naval Air Warfare Center, China Lake, California, USACorrespondence[email protected]
Pages 3903-3908 | Received 08 Apr 2008, Published online: 20 Oct 2008
 
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Abstract

The alkylation of 4-methoxyphenol with 2-ethylhexyl bromide was accelerated by using potassium tert-butoxide in dimethylformamide. Subsequent chloromethylation occurred quickly using acetic acid as a cosolvent to give the poly[(2-(2-ethylhexyloxy)-5-methoxy-p-phenylene)vinylene] (MEH-PPV) monomer in 61% overall yield on a 2-mol scale.

ACKNOWLEDGMENTS

The financial support of the Environmental Security Technology Certification Program Project Number WP-0527 managed by Dr. Bruce D. Sartwell is gratefully acknowledged. Thanks to Drs. Jennifer A. Irvin and David J. Irvin (China Lake) for kindly supplying 2-ethylhexyl bromide.

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