Addition of Chloromethyl Methyl Ether to Isoprene and the Prepation of Isogeranyl Methyl Ether
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- SATO Toru
- Industrial Research Institute of Kanagawa Prefecture
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- KISE Hideo
- Institute of Industrial Science, University of Tokyo
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- SENO Manabu
- Institute of Industrial Science, University of Tokyo
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- ASAHARA Teruzo
- Institute of Industrial Science, University of Tokyo
Bibliographic Information
- Other Title
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- イソプレンに対するクロロメチルメチルエーテルの付加反応とイソゲラニルメチルエーテルの合成
- イソプレン ニ タイスル クロロメチルメチルエーテル ノ フカ ハンノウ ト
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Description
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.
Journal
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- Journal of Japan Oil Chemists' Society
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Journal of Japan Oil Chemists' Society 24 (9), 607-610, 1975
Japan Oil Chemists' Society
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Details 詳細情報について
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- CRID
- 1390282680308628224
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- NII Article ID
- 130001012349
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- NII Book ID
- AN00245435
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- ISSN
- 0513398X
- 18842003
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- NDL BIB ID
- 1621404
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- Data Source
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- JaLC
- NDL
- Crossref
- CiNii Articles
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- Abstract License Flag
- Disallowed