- PROCESSES FOR PREPARING 2-ISOPROPENYL-5-METHYL-4-HEXENOIC ACID, 2-ISOPROPENYL-5-METHYL-4-HEXEN-1-OL, AND A CARBOXYLATE ESTER THEREOF
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The present invention provides a process for preparing 2-isopropenyl-5-methyl-4-hexenoic acid of the following formula (4), comprising steps of: subjecting a Grignard reagent of the following general formula (1), wherein R1 represents a linear, branched, or aromatic monovalent hydrocarbon group having 1 to 8 carbon atoms, and X represents a chlorine atom, a bromine atom, or an iodine atom, and 1,1,1,3,3,3-hexamethyldisilazane to a deprotonation reaction to form a 1,1,1,3,3,3-hexamethyldisilazane derivative; and subjecting 2-methyl-3-buten-2-yl 3-methyl-2-butenoate of the following formula (3) to a rearrangement reaction in the presence of the 1, 1, 1,3,3,3-hexamethyldisilazane derivative to form 2-isopropenyl-5-methyl-4-hexenoic acid (4).
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- METHOD FOR PRODUCING 2-ISOPROPENYL-5-METHYL-4-HEXEN-1-YL 3-METHYL-2-BUTENOATE
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Provided is a method for industrially producing 2-isopropenyl-5-methyl-4-hexen-1-yl 3-methyl-2-butenoate, which is, for example, a sex pheromone substance of vine mealybug. More specifically, there is provided a method for producing 2-isopropenyl-5-methyl-4-hexen-1-yl 3-methyl-2-butenoate, comprising a step of transesterifying 2-isopropenyl-5-methyl-4-hexen-1-ol represented by Formula (1) with alkyl senecioate represented by General Formula (2) in the presence of a catalyst, while distilling off an alcohol represented by General Formula (4) formed as a by-product, to obtain 2-isopropenyl-5-methyl-4-hexen-1-yl 3-methyl-2-butenoate represented by Formula (3).
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Page/Page column 0057
(2016/06/28)
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- PROCESS FOR PRODUCING 2-ISOPROPENYL-5-METHYL-4-HEXENE-1-YL- 3-METHYL-2-BUTENOATE
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Provided is a method capable of solving the problems associated with production of LVSA, which is a pheromone produced by female pest mealybugs, and is useful as an agrochemical pest, at an industrial large scale, and producing LVSA in a high yield. Specifically, the present invention provides a production method of 2-isopropenyl-5-methyl-4-hexen-1-yl 3-methyl-2-butenoate, comprising reacting senecioic acid with a halogenating agent to give senecioic acid halide, reacting the obtained senecioic acid halide with 2-isopropenyl-5-methyl-4-hexen-1-ol in the presence of an organic base compound and heat treating the obtained crude 2-isopropenyl-5-methyl-4-hexen-1-yl 3-methyl-2-butenoate in the presence of a basic substance at 50 - 250°C.
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Page/Page column 5
(2009/12/05)
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- METHOD FOR PRODUCING 2-ISOPROPENYL-5-METHYL-4-HEXEN-1-YL 3-METHYL-2-BUTENOATE
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Disclosed is a method for commercially advantageously producing 2-isopropenyl-5-methyl-4-hexen-1-yl 3-methyl-2-butenoate with high yield. Specifically disclosed is a method for producing 2-isopropenyl-5-methyl-4-hexen-1-yl 3-methyl-2-butenoate represented by the formula (IV) below which is characterized in that a sulfonate compound represented by the general formula (III) below is obtained by reacting 2-isopropenyl-5-methyl-4-hexen-1-ol with an organic sulfonyl halide in the presence of a basic substance, and then the thus-obtained sulfonate compound is reacted with a senecioic acid in the presence of a basic substance. (In the formula, R represents a hydrocarbon group.)
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Page/Page column 8
(2008/06/13)
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- Identification and synthesis of the sex pheromone of the vine mealybug, Planococcus ficus
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Sexually mature females of an important agricultural pest, the vine mealybug Planococcus ficus, produce the monoterpene (S)-lavandulol and the corresponding ester, (S)-(+)-lavandulyl senecioate. The racemic ester was highly attractive to mature male mealy
- Hinkens, Diane M.,McElfresh, J. Steven,Millar, Jocelyn G.
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p. 1619 - 1621
(2007/10/03)
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