Preparation of Methyl Substituted Phenyl Ethers from Aromatic Primary Amines

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  • 芳香族第一アミンからメチルフェニルエーテル類の合成
  • ホウコウゾク ダイイチ アミン カラ メチルフェニルエーテルルイ ノ ゴウセイ

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In order to obtain methyl aryl ethers, the diazonium compounds of toluidines, nitroanilines and chloroanilines were decomposed in methanol.<BR>The effects of kinds of acids, concentration of acid, catalysts, illumination with UV light and reaction temperature on diazotization and decomposition of the diazonium compounds in methanol were examined.<BR>Sulfuric acid was preferred for the diazotization and the decomposition. The concentration of sulfuric acid the reaction mixture was suitable in the range of 0.5 to 5%.<BR>The best yield was obtained at 65°Cof the decomposition temperature. While the illumination of UV light affected the preparation of dimethoxy benzenes from anisidines as described in the privious studies, it was not effective for the preparation of methyl aryl ethers from theses amines.<BR>Nickel sulfate was effective as the catalyst in the case of p-toluidine. But no catalyst was effective in the case of other amines.<BR>The maximum yields obtained were as follows; methylanisoles (o-48.5%, m-65.0%, p-79.5%) nitroanisoles (o-21.5%, p-26.5%) and chloroanisoles (o-1.0%, m-37.5%, p-31.4%). m-Nitroanisole was not obtained from the corresponding amine.

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