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anisole

Product name anisole
Synonyms methoxybenzene
methylphenyl ether
GOST no data
CAS 100-66-3

Anisole C6H5OCH3 is a clear, colorless liquid with a pleasant smell similar to that of anise seed. It has a good solubility in ethanol, diethyl ether, benzene, toluene, chloroform and most organic solvents. It is poorly soluble in water (1.5g/l). Due to inductive effect of methoxy group upon the aromatic ring, anisole reacts with electrophiles in the electrophilic aromatic substitution reaction more quickly than benzene. Being chlorinated, it forms the mixture of 4-chloro-, 2,4-dichloro- and 2,4,6-trichloroanisoles. Anisole reacts with acetic anhydride or acetyl chloride to give 4-methoxyacetophenone.

Production.

Commercially anisole is prepared:

  • by interaction of sodium phenolate with sodium methanesulfonate:

    C6H5ONa + CH3OSO2ONa --> C6H5OCH3 + Na2SO4

  • by phenol alkylation with methyl alcohol at 175-225°C in phe presence of aluminium oxide Al2O3:

    C6H5OH + CH3OH --> C6H5OCH3 + H2O

    Uses.

    Anisole is used:

  • as a solvent;
  • as an intermediate in making of dyes, pharmaceuticals, fragnances;
  • as an insect pheromone;

  • Manufacturer(s) OJSC AROMASYNTHEZ
    Chemical structure of anisole

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