Synthesis of cinnamyl ethers from α-vinylbenzyl alcohol using iodine as catalyst.
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.
Kasashima
Yoshio
Y
Education Center, Faculty of Engineering, Chiba Institute of Technology, Chiba, Japan. yoshio.kasashima@it-chiba.ac.jp
Uzawa
Atsushi
A
Hashimoto
Kahoko
K
Nishida
Tadasuke
T
Murakami
Keiko
K
Mino
Takashi
T
Sakamoto
Masami
M
Fujita
Tsutomu
T
D002219:Carbamates / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D004987:Ethers / Q000138:chemical synthesis* / Q000737:chemistry; D007455:Iodine / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy / Q000592:standards; D015394:Molecular Structure; D020005:Propanols / Q000737:chemistry*; D012015:Reference Standards; D013237:Stereoisomerism
D002219:Carbamates; D004987:Ethers; D020005:Propanols; D007455:Iodine