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Allyl phenyl ether

Allyl phenyl ether is an organic compound with the formula C<sub>6</sub>H<sub>5</sub>OCH<sub>2</sub>CH=CH<sub>2</sub>. It is a colorless solid.

Preparation

Allyl phenyl ether is prepared by the reaction of sodium phenoxide with allyl bromide:

C<sub>6</sub>H<sub>5</sub>ONa + BrCH<sub>2</sub>CH=CH<sub>2</sub> → C<sub>6</sub>H<sub>5</sub>OCH<sub>2</sub>CH=CH<sub>2</sub> + NaBr

The 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.

References