以碘为催化剂，由α-乙烯基苄醇合成肉桂基醚。

Synthesis of cinnamyl ethers from α-vinylbenzyl alcohol using iodine as catalyst.

作者信息

Kasashima Yoshio, Uzawa Atsushi, Hashimoto Kahoko, Nishida Tadasuke, Murakami Keiko, Mino Takashi, Sakamoto Masami, Fujita Tsutomu

机构信息

Education Center, Faculty of Engineering, Chiba Institute of Technology, Chiba, Japan.

出版信息

J Oleo Sci. 2010;59(10):549-55. doi: 10.5650/jos.59.549.

DOI:10.5650/jos.59.549

PMID:20877148

Abstract

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.

摘要

研究了以碘为催化剂时，α-乙烯基苄醇与其他醇类的反应。得到了相应的肉桂基醚作为产物。这表明α-乙烯基苄醇通过1-苯基烯丙基阳离子转化为肉桂基醚。在以下条件下，α-乙烯基苄醇与乙醇在乙腈中与碘反应，以75%的产率得到肉桂基乙醚：温度 = 50 °C，α-乙烯基苄醇:乙醇:碘的摩尔比 = 1:3.0:0.2，反应时间 = 6 h。一般来说，使用伯醇的反应产率高于使用仲醇和叔醇的反应产率。α-乙烯基苄醇与碘的反应也会发生醚交换，但只有当烯丙基用作起始醚的另一个取代基时，反应才能顺利进行。