Synthesis of Cinnamyl Ethers from α-Vinylbenzyl Alcohol Using Iodine as Catalyst

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概要

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• Reactions of α-vinylbenzyl alcohol with other alcohols using iodine as a catalyst were investigated. The corresponding cinnamyl ethers were obtained as products. This suggested that α-vinylbenzyl alcohol was converted to cinnamyl ethers via 1-phenylallyl cation. Cinnamyl ethyl ether was obtained in 75% yield by the reaction of α-vinylbenzyl alcohol and ethanol in acetonitrile with iodine under the following conditions: temperature = 50 °C, molar ratio of α-vinylbenzyl alcohol:ethanol:iodine = 1:3.0:0.2, and time period = 6 h. Generally, the yields of the reactions using primary alcohols were higher than those using secondary and tertiary alcohols. Ether interchange also occurred by the reaction of α-vinylbenzyl alcohol and iodine, but proceeded smoothly only when an allyl group was used as the other substituent of the starting ether.

著者

• Mino Takashi

  Graduate School Of Engineering Chiba Univ.

• Fujita Tsutomu

  Graduate School Of Engineering Chiba Univ.

• Sakamoto Masami

  Graduate School Of Engineering Chiba Univ.

• HASHIMOTO Kahoko

  Department of Life and Environmental Sciences and High Technology Research Center, Chiba Institute o

• Kasashima Yoshio

  Education center, Faculty of engineering, Chiba Institute of Technology

• Uzawa Atsushi

  Education Center, Faculty of Engineering, Chiba Institute of Technology

• Nishida Tadasuke

  Graduate School of Science and Technology, Chiba University

• Murakami Keiko

  Graduate School of Engineering, Chiba University

• Mino Takashi

  Graduate School of Engineering, Chiba University

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