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

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.

Carboxymethylation of cinnamylalcohol with dimethyl carbonate over the slag-based catalysts

“…The base nature of the catalysts results in allyl rearrangement of cinnamylalcohol into vinylbenzyl alcohol (reaction 11), which is a backward reaction of the one reported in [50]. Obtained vinylbenzyl alcohol reacts with preferably DMC due to its excess and also with formed methanol according to reactions 12 and 13, respectively.…”

Metal Triflate-Promoted Allylic Substitution Reactions of Cinnamyl Alcohol in the Presence of Orthoesters and Acetals

“…GC–MS analysis was performed in EI mode using a Varian 450GC and Varian 300MS employing a VF-5 ms capillary column (30 m, 0.25 mm i.d., and 0.25 μm) operating with a gradient temperature profile with an initial temperature of 50 °C for 3 min rising to 280 °C at a rate of 20 °C min –1 followed by a 3 min hold time. All products gave spectroscopic data consistent with previous literature reports. ,,, …”

“…All products gave spectroscopic data consistent with previous literature reports. 21,28,29,48 Typical Procedure for the Allylic Substitution Reaction of Cinnamyl Alcohol with TEOF. Indium triflate (14 mg, 0.025 mmol, 5 mol %) was added to a solution of cinnamyl alcohol (67 mg, 0.5 mmol) and TEOF (75 mg, 0.5 mmol) in chloroform (2 mL) at room temperature and stirred for 15 min.…”