Alkyl aryl ethers

Structure of anisole

Alkyl aryl ethers are a group of organic chemical compounds . They are ethers which on the one hand carry an alkyl radical and on the other hand an aryl radical on their oxygen bridge . Its representatives include, for example, the phytonutrients anisole , anethole and asarone as well as phenetole . Anisole belongs to the subgroup of the alkyl phenyl ethers .

Presentation and extraction

Alkyl aryl ethers can be produced, for example, by the Williamson ether synthesis . For this purpose, the sodium salt of the aryl compound (for example sodium phenolate ) is reacted with alkyl halides , preferably iodides :

${\displaystyle \mathrm {C_{6}H_{5}{-}ONa\ +\ CH_{3}{-}I\longrightarrow \ C_{6}H_{5}{-}O{-}CH_{3}\ +\ NaI} }$

Reaction between sodium phenate and methyl iodide to form anisole and sodium iodide

On an industrial scale, dialkyl sulfates (for example diethyl sulfate to introduce ethyl residues ) can also be used instead of the alkyl halides :

${\displaystyle \mathrm {C_{6}H_{5}{-}ONa\ +\ (H_{3}CO)_{2}{-}SO_{2}\longrightarrow \ C_{6}H_{5}{-}O{-}CH_{3}\ +\ (H_{3}CO)SO_{3}Na} }$

Reaction between sodium phenolate and dimethyl sulfate to form anisole.

Individual evidence

• H. Beyer et al. W. Walter: Textbook of Organic Chemistry . 20th ed., Hirzel, Stuttgart 1984. pp. 463-464.