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Processes for preparing 2-isopropenyl-5-methyl-4-hexenoic acid, 2-isopropenyl-5-methyl-4-hexen-1-ol, and a carboxylate ester thereof

一种异丙烯基、己烯酸的技术，应用在羧酸酯制备、羧酸酯/内酯制备、羧酸酰卤制备等方向，能够解决天然风味影响等问题

Active Publication Date: 2021-10-22
SHIN ETSU CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] This promiscuous 2-isopropylidene-5-methyl-4-hexen-1-ol may affect the Effect of natural flavor, and adverse effect of inhibiting the function of 2-isopropenyl-5-methyl-4-hexen-1-ylcarboxylate as a sex pheromone component of mealybug

Method used

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  • Processes for preparing 2-isopropenyl-5-methyl-4-hexenoic acid, 2-isopropenyl-5-methyl-4-hexen-1-ol, and a carboxylate ester thereof
  • Processes for preparing 2-isopropenyl-5-methyl-4-hexenoic acid, 2-isopropenyl-5-methyl-4-hexen-1-ol, and a carboxylate ester thereof
  • Processes for preparing 2-isopropenyl-5-methyl-4-hexenoic acid, 2-isopropenyl-5-methyl-4-hexen-1-ol, and a carboxylate ester thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0171] The present invention will be further described with reference to the following Synthesis Examples, Examples and Comparative Examples. It should be understood that the present invention is not limited or limited by these examples.

[0172] Unless otherwise specified, the term "purity" as used herein refers to area percent in gas chromatography (hereinafter also referred to as "GC"). The term "production ratio" refers to the ratio of area percentages in a GC.

[0173] The term "yield" is calculated based on area percent determined by GC.

[0174] Taking into account the purity (%GC) of the starting material and product, the yield was calculated according to the following equation.

[0175] Yield (%)={[(weight of product obtained by reaction×%GC) / molecular weight of product]÷[(weight of starting material in reaction×%GC) / molecular weight of starting material]}×100

[0176] The term "conversion" is calculated from the sum of the area percentages of the starting material...

Synthetic example 1

[0184] Synthesis Example 1: Preparation of 2-methyl-3-buten-2-yl 3-methyl-2-butenoate (3)

[0185]

[0186] The air in the reactor equipped with a stirrer, condenser and thermometer was purged with nitrogen. Then, 3-methyl-2-butenoic acid (100.1 g: 1.00 mol), p-toluenesulfonyl chloride (247.9 g: 1.30 mol) and toluene (300.0 g) were added to the reactor, and heated to 50°C. Pyridine (300.6 g: 3.8 mol) was added dropwise to the reaction mixture for 2 hours at a reaction mixture temperature of 50°C to 60°C. After the dropwise addition was complete, the reaction mixture was stirred at a reaction mixture temperature of 60°C for 1 hour. Then, 2-methyl-3-buten-2-ol (103.4 g: 1.2 mol) was added dropwise to the reaction mixture over 1 hour at a reaction mixture temperature of 65°C to 70°C. The reaction mixture was then stirred at a reaction mixture temperature of 68°C to 70°C for 8 hours. Then, the temperature of the reaction mixture was lowered to 55 to 60°C. Water (185.0 g) wa...

Synthetic example 2

[0192] Synthesis Example 2: Preparation of 2-methyl-3-buten-2-yl 3-methyl-2-butenoate (3)

[0193]

[0194] The procedure of Synthesis Example 1 was repeated except that benzenesulfonyl chloride (229.6 g: 1.30 mol) was used instead of p-toluenesulfonyl chloride to obtain 2-methyl-3-buten-2-yl3-methyl-2- Butenoate (3) (149.7 g: 0.89 mol, yield 89.1%, purity 95.5%).

[0195] Various spectral data of the thus prepared 2-methyl-3-buten-2-yl 3-methyl-2-butenoate (3) were the same as those obtained in Synthesis Example 1.

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Abstract

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 R<1> 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).

Description

technical field [0001] The present invention relates to a process for the preparation of 2-isopropenyl-5-methyl-4-hexenoic acid, 2-isopropenyl-5-methyl-4-hexen-1-ol and their carboxylic acid esters. Background technique [0002] 2-Isopropenyl-5-methyl-4-hexen-1-ol (collectively: lavender alcohol) is known as a fragrance component of lavender oil and lavender hybrid oil, and is widely used as a fragrance in cosmetics and perfumes. Natural essential oils contain their (R)-optical isomers and have a herbal citrus flavor. Meanwhile, its (S)-optical isomer has only a weak odor. Therefore, mixtures of optical isomers can be chemically synthesized at lower cost. [0003] 2-Isopropenyl-5-methyl-4-hexen-1-ylcarboxylate is reported to be a component of the sex pheromone of mealybugs, such as the grape mealybug (scientific name: Planococcus ficus )) (the following non-patent document 1), Banana mealybug (scientific name: Dysmicoccus grassii) (the following non-patent document 2), pi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C51/09C07C57/03C07C29/147C07C33/02C07C67/08C07C69/533C07F7/10C07F3/02
CPCC07C51/09C07C29/147C07C67/08C07F7/10C07F3/02C07C57/03C07C33/02C07C69/533C07C67/00C07C67/14C07C67/03C07C69/24C07C69/145
Inventor 山下美与志金生刚
Owner SHIN ETSU CHEM CO LTD
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