Toru Sato, H. Kise, M. Senō
Sep 20, 1975
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Journal
Journal of Japan Oil Chemists Society
Abstract
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.