Anisole, also known as methoxybenzene, is a clear, colorless liquid with a pleasant smell similar to that of anise seed. Anisole is more electron rich than benzene because of the resonance effect of the methoxy group upon the aromatic ring. This resonance effect has a greater effect upon the π cloud of the ring than the inductive effect where the electronegative oxygen exerts a pull on the electron density in the benzene ring through the sigma bond.

Anisole reacts with electrophiles in the aromatic electrophilic substitution reaction more quickly than benzene, which is turn reacts more quickly than nitrobenzene.

Rate of reaction

Anisole > Benzene > Nitrobenzene

The methoxy group acts as a ortho/para directing group.

Anisole is used in perfumery, in chemical syntheses, and is an insect pheromone.

Anisole reacts with acetic anhydride to give 4-Methoxyacetophenone and acetic acid as a byproduct. The reaction of anisole with P_{4S10 forms Lawesson's reagent an important chemical in phosphorus-sulfur chemistry.}

See also

• Ether
• Phenol
• 2,4,6-Trichloroanisole (cork taint)
• Anethole

External links

• Pherobase pheromone database entry

Ethers | Aromatic compounds | Pheromones

Anisol