Synthesis of Dibenzyl Ethers Using Phase-Transfer Catalysis

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  • KODOMARI MARIO
    Department of Industrial Chemistry, Shibaura Institute of Technology
  • SAWAMURA Masayuki
    Department of Industrial Chemistry, Shibaura Institute of Technology
  • KUBO Naoya
    Department of Industrial Chemistry, Shibaura Institute of Technology
  • YOSHITOMI Suehiko
    Department of Industrial Chemistry, Shibaura Institute of Technology

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Other Title
  • 相間移動触媒によるジベンジルエーテル類の合成

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Description

Formation of dibenzyl ether in the phase-transfer-catalyzed reaction of benzyl chloride with aqueous sodium hydroxide was examined. Benzyl chloride and catalytic amounts of methyl-trioctylammonium chloride(TOMAC) in 50% aq. NaOH were .stirred at 70°C for 1 hour to form dibenzyl ether in 98% yield. The rate of formation of dibenzyl ether increased with increase of the concentration of aq. NaOH., TOMAC, tetrabutylammonium chloride and tetraoctyl-ammonium bromide were the most effective among the quaternary ammonium salts. Ammonium salts bearing the benzyl group and the phosphonium salts were less effective. The correspond-ing dibenzyl ethers were also obtained in good yield from the substituted benzyl chlorides under the same conditions. o-Methylbenzyl chloride was more reactive than p- and m-isomers.

Journal

  • NIPPON KAGAKU KAISHI

    NIPPON KAGAKU KAISHI 1980 (1), 58-61, 1980-01-10

    The Chemical Society of Japan

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