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Journal of oleo science

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


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.

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423769
α-Vinylbenzyl alcohol, 97%
C9H10O