23960-07-8

Upstream product

• 541-47-9 3-Methylbutenoic acid 
• 912841-61-3 2-isopropenyl-5-methyl-4-hexen-1-yl methanesulfonate 
• 21634-59-3 2-methyl-3-buten-2-yl 3-methyl-2-butenoate 
• 497-67-6 2-(1-methylethenyl)-5-methyl-4-hexenoic acid 
• 58461-27-1 (+/-)-lavandulol 
• 924-50-5 Methyl 3,3-dimethylacrylate 
• 3350-78-5 3,3-Dimethylacryloyl chloride 

Relevant academic research and scientific papers

PROCESSES FOR PREPARING 2-ISOPROPENYL-5-METHYL-4-HEXENOIC ACID, 2-ISOPROPENYL-5-METHYL-4-HEXEN-1-OL, AND A CARBOXYLATE ESTER THEREOF

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).

METHOD FOR PRODUCING 2-ISOPROPENYL-5-METHYL-4-HEXEN-1-YL 3-METHYL-2-BUTENOATE

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).

PROCESS FOR PRODUCING 2-ISOPROPENYL-5-METHYL-4-HEXENE-1-YL- 3-METHYL-2-BUTENOATE

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.

METHOD FOR PRODUCING 2-ISOPROPENYL-5-METHYL-4-HEXEN-1-YL 3-METHYL-2-BUTENOATE

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.)

Identification and synthesis of the sex pheromone of the vine mealybug, Planococcus ficus

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