Citronellyl ester compound, preparation method thereof and spice

A compound, a technology of citronellyl ester, applied in the field of spices, citronellyl ester compounds and preparation methods thereof, can solve the problems of singleness and can not meet the needs of consumers and the like

Active Publication Date: 2020-06-19
DONGGUAN BOTON FLAVORS & FRAGRANCES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] In recent years, with the diversification of various food ingredients, food additives, beverages, food, cosmetics, health care materials, etc., the new de

Method used

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  • Citronellyl ester compound, preparation method thereof and spice
  • Citronellyl ester compound, preparation method thereof and spice
  • Citronellyl ester compound, preparation method thereof and spice

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preparation example Construction

[0028] The preparation method of the citronellyl ester compound of above-mentioned embodiment, comprises the following steps:

[0029] S110: Under the condition of continuously feeding anhydrous hydrogen chloride gas, mixing 5-hydroxyvaleraldehyde and chloroform to perform a hemiacetal reaction to obtain 2-hydroxytetrahydropyran;

[0030] Wherein the structural formula of 5-hydroxypentanal is The structural formula of 2-hydroxytetrahydropyran is

[0031] The chemical reaction equation of step S110 is as follows:

[0032]

[0033] Wherein, chloroform is used as a solvent to dissolve 5-hydroxypentanal, and anhydrous hydrogen chloride is used as a catalyst.

[0034] Specifically, the above hemiacetal reaction is carried out at a reaction temperature of 50° C. to 70° C. for 2 hours to 4 hours. In a specific example, the reaction temperature may be 50°C, 55°C, 60°C or 70°C, and the reaction time may be 2h, 3h or 4h. Appropriate reaction temperature and time can make the r...

Embodiment 1

[0080] The preparation method of the citronellyl compound of the present embodiment may further comprise the steps:

[0081] 1) Preparation of 2-hydroxytetrahydropyran

[0082] Add 51g of 5-hydroxyvaleraldehyde and 100mL of chloroform to the three-necked flask, while continuously feeding anhydrous hydrogen chloride gas, heating to 60°C, and reacting for 3h; the reacted product is distilled under reduced pressure and collected under a pressure of 300Pa The mother liquor temperature is 50 ℃~70 ℃ distillate, obtains 46g colorless transparent viscous oil product 2-hydroxytetrahydropyran;

[0083] 2) Preparation of 4-(2-oxyl-tetrahydropyran)butanol

[0084] 46g 2-hydroxytetrahydropyran, 41g 1,4-butanediol, 125mL tetrahydrofuran (THF), 153g triphenylphosphine (PPh 3 ), and cooled to 0°C, slowly add 136g of diisopropyl azodicarboxylate dropwise, and stir the reaction at room temperature for 12h after the dropwise addition; the product after the reaction is subjected to vacuum disti...

Embodiment 2

[0097] The preparation method of the citronellyl compound of the present embodiment may further comprise the steps:

[0098] 1) Preparation of 2-hydroxytetrahydropyran

[0099] Add 45g of 5-hydroxyvaleraldehyde and 900mL of chloroform to the three-necked flask, while continuously feeding anhydrous hydrogen chloride gas, heating to 70°C, and reacting for 2h; the reacted product is distilled under reduced pressure and collected under a pressure of 300Pa The mother liquor temperature is 50 ℃~70 ℃ distillate, obtains 37g colorless transparent viscous oil product 2-hydroxytetrahydropyran;

[0100] 2) Preparation of 4-(2-oxyl-tetrahydropyran)butanol

[0101] Add 37g 2-hydroxytetrahydropyran, 32g 1,4-butanediol, 100mL tetrahydrofuran THF, 148g triphenylphosphine (PPh 3 ), and cooled to 2°C, slowly added dropwise 144g of diisopropyl azodicarboxylate, stirred and reacted at room temperature for 10h after the dropwise addition; the product after the reaction was distilled under reduce...

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Abstract

The invention relates to a citronellyl ester compound, a preparation method thereof and spice. The preparation method of the compound comprises the following steps of performing Mitsunobu reaction on2-hydroxytetrahydropyran and 1, 4-butanediol, preparing 4-(2-oxy-tetrahydropyrane) butanol, oxidizing the 4-(2-oxy-tetrahydropyrane) butanol into 4-(2-oxy-tetrahydropyrane) butyric acid, and performing esterification reaction on the 4-(2-oxy-tetrahydropyrane) butyric acid and rhodinol to prepare a citronellol ester compound 4-(2-oxy-tetrahydropyrane) butyrate-3, 7-dimethyl-6-octenyl ester. The compound still has animal musk while having jasmine fragrance, is long in fragrance lasting time, and is widely applied to the field of flavor blending.

Description

technical field [0001] The invention relates to the technical field of perfumes, in particular to citronellyl ester compounds, a preparation method thereof and perfumes. Background technique [0002] In recent years, with the diversification of various food ingredients, food additives, beverages, food, cosmetics, health care materials, etc., the new demand for spices used in them is increasing. The compounds currently prepared usually only have aroma, which is too Single, can not meet the needs of consumers. Contents of the invention [0003] Based on this, it is necessary to provide a citronellol compound having both jasmine and animal musk. [0004] A kind of citronellal ester compound, the structural formula of described compound is as shown in formula (I): [0005] [0006] Further, a kind of preparation method of citronellyl ester compound is also provided, comprising the following steps: [0007] 2-Hydroxytetrahydropyran and 1,4-butanediol are subjected to Mits...

Claims

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Application Information

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IPC IPC(8): C07D309/12C11B9/00
CPCC07D309/12C11B9/008
Inventor 蔡国祥钟能帮关俊健吴奇林胡仕林冯娇
Owner DONGGUAN BOTON FLAVORS & FRAGRANCES
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