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

• Autores: Elizabeth M. Sanford, Christina C. Lis, Nikolas R. McPherson
• Localización: Journal of chemical education, ISSN 0021-9584, Vol. 86, Nº 12 (December), 2009, págs. 1422-1423
• Idioma: inglés
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• Resumen

  • 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 pKa 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.