イソプレンに対するクロロメチルメチルエ-テルの付加反応とイソゲラニルメチルエ-テルの合成

概要

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The cationic addition of chloromethyl methyl ether to isoprene in the presence of metal halides was investigated in order to obtain the 1, 4-adduct, 1-chloro-3-methyl-5-methoxypentene-2. It was found that the addition of small amounts of ethyl alcohol caused a large increase in the yield of the adduct, especially in the case of stannic chloride catalyst. Aliphatic glycols and esters as well as alcohols were found to be effective cocatalysts. A reaction mechanism of the cationic telomerization was discussed and the effects of the additives were attributed to the intramolecular chloride transfer in the reaction intermediate, [CH3OCH2 (C5H8)] + [SnCl5] - [ROH] x. The Grignard coupling of 1-chloro-3-methyl-5-methoxypentene-2 with methallyl chloride afforded α-isogeranyl methyl ether, a useful component of mixed perfumes.
日本油化学会の論文