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The Preparation of Allyl Phenyl Ether and 2-Allylphenol Using the Williamson Ether Synthesis and Claisen Rearrangement

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Elizabeth M. Sanford , Christina C. Lis and Nikolas R. McPherson

Department of Chemistry, Hope College, Holland, MI 49422-9000

J. Chem. Educ., 2009, 86 (12), p 1422

DOI: 10.1021/ed086p1422

Publication Date (Web): December 1, 2009

Abstract

Ether chemistry is essential to organic synthesis. The Williamson ether synthesis of allyl phenyl ether and its subsequent Claisen rearrangement to 2-allylphenol introduces two important reactions of ethers to the undergraduate laboratory. Purification is accomplished using acid–base extraction, which reinforces understanding of the pK_a differences between aliphatic and aromatic alcohols. The ¹H NMR spectrum of allyl phenyl ether is used to introduce the extraction of coupling constants and the interpretation of complex splitting patterns for structure determination.

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Received: August 03, 2009

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Article

The Preparation of Allyl Phenyl Ether and 2-Allylphenol Using the Williamson Ether Synthesis and Claisen Rearrangement