Allyl phenyl ether explained

Allyl phenyl ether is an organic compound with the formula C₆H₅OCH₂CH=CH₂. It is a colorless solid.

Preparation

Allyl phenyl ether is prepared by the reaction of sodium phenoxide with allyl bromide:^[1]

C₆H₅ONa + BrCH₂CH=CH₂ → C₆H₅OCH₂CH=CH₂ + NaBrThe yield is almost quantitative when the reaction is conducted in homogeneous solution using dimethoxyethane. When the reaction is conducted as a slurry in diethyl ether, the predominant product is, after acidic work-up, 2-allylphenol.

Reactions

Allyl phenyl ether converts to 2-allylphenol in the presence of acid catalysts. This conversion is an example of the Claisen rearrangement.^{[2] [3]}

Notes and References

1. 10.1021/ja01520a030. Heterogeneity as a Factor in the Alkylation of Ambident Anions: Phenoxide Ions1,2. 1959. Kornblum. Nathan. Lurie. Arnold P.. Journal of the American Chemical Society. 81. 11. 2705–2715.
2. 10.1021/cr020703u. Claisen Rearrangement over the Past Nine Decades. 2004. Martín Castro. Ana M.. Chemical Reviews. 104. 6. 2939–3002. 15186185.
3. Yadav, G. D.; Lande, S. V., UDCaT-5: A Novel and Efficient Solid Superacid Catalyst for Claisen Rearrangement of Substituted Allyl Phenyl Ethers. Synthetic Communications 2007, 37 (6), 941-946