Hyacinth aroma compound, preparation method thereof and hyacinth aroma base

Abstract

The invention relates to the technical field of flavors and fragrances, in particular to a hyacinth aroma compound, a preparation method thereof and a hyacinth aroma base, the hyacinth aroma compound has the following structural formula: # imgabs0 #, the hyacinth aroma compound is 4-(((3-methyl-2-butene-1-yl) oxy) methyl) phenylpropanal, and the structural formula of the hyacinth aroma compound is 4-(((3-methyl-2-butene-1-yl) oxy) methyl) phenylpropanal. The hyacinth essence has the remarkable flower fragrance characteristic of hyacinth and has the advantages of being obvious in fragrance, high in molecular weight, long in fragrance holding time, good in stability and the like. The preparation method of the hyacinth aroma compound is high in production efficiency, convenient to control and beneficial to industrial production. By adding the hyacinth aroma compound, the hyacinth aroma type essence base has the obvious hyacinth flower aroma type characteristic, the aroma is obvious, the aroma holding time is long, and the stability is good.

Description

Technical Field

[0001] The invention relates to the technical field of chemical industry, and in particular to a hyacinth aroma compound and a preparation method thereof and a hyacinth aroma base. Background Art

[0002] Hyacinthus is a perennial bulbous plant of the genus Hyacinthus in the Liliaceae family. It is widely planted in China. It is not only used as an ornamental plant, but also loved by people for its fragrant aroma. The aroma of hyacinth is usually described as fresh, sweet, rich and elegant. This fragrance is most intense in late spring and early summer. Whenever the hyacinth flowers bloom, its fragrance can drift with the wind, giving people a pleasant enjoyment. The fragrance of hyacinth also has the effects of soothing emotions and improving sleep, and is used in aromatherapy. Therefore, hyacinth flavor has important uses and is widely used in various detergents, cosmetics, air fresheners and other daily chemical products. Some compounds commonly used in existing hyacinth flavors, such as phenylethyl alcohol, phenylpropanol, cinnamyl alcohol, etc., all have slight hyacinth aroma characteristics. These compounds have a small molecular weight and good volatility, and usually have good performance in the top fragrance of the fragrance. However, as they evaporate and dissipate, their aroma is insufficient in the body fragrance and base fragrance of the fragrance, resulting in the richness and naturalness of the hyacinth fragrance itself being out of balance over time. Moreover, the hyacinth aroma characteristics of these compounds are not prominent, and they are more rose and sweet. Therefore, it is of great significance to develop a hyacinth-scented compound that has a significant hyacinth floral aroma characteristic, a long lasting fragrance, good stability, and a wide range of applications. Summary of the invention

[0003] In order to overcome the shortcomings and deficiencies in the prior art, the present invention aims to provide a hyacinth aroma compound and a preparation method thereof, wherein the compound has a significant hyacinth floral fragrance characteristic, has a significant fragrance, a high molecular weight, a long fragrance retention time, and good stability, and has important and advantageous uses in the field of perfumery. The preparation method of the hyacinth aroma compound has high production efficiency, is easy to control, and is conducive to industrial production.

[0004] Another object of the present invention is to provide a hyacinth-flavored fragrance base, which has significant hyacinth floral fragrance characteristics by adding hyacinth aroma compounds, has obvious fragrance, long lasting fragrance time and good stability.

[0005] The purpose of the present invention is achieved through the following technical solution: A hyacinth aroma compound has the following structural formula:

[0006]

[0007] The hyacinth aroma compound can be named as: 4-(((3-methyl-2-buten-1-yl)oxy)methyl)phenylpropanal.

[0008] The hyacinth aroma compound of the present invention has a significant hyacinth flower fragrance characteristic, and has an important and advantageous use in the field of perfume adjustment due to its obvious fragrance, high molecular weight, long fragrance retention time and good stability. It can be used in soaps, detergents, skin care products, air fresheners and other daily chemical products, and can also be used for perfume addition of paper, plastics, leather, fabrics and the like. The compound can be used to prepare a fragrance base, and then the fragrance base is prepared into a daily chemical essence, and can also be directly used as a raw material for preparing a daily chemical essence.

[0009] The present invention also provides a method for preparing a hyacinth aroma compound, comprising the following steps:

[0010] Step 1: Use 4-iodobenzyl alcohol to prepare ((4-iodobenzyl)oxy)triisopropylsilane. The structural formula of ((4-iodobenzyl)oxy)triisopropylsilane is shown below:

[0011]

[0012] Step 2: Use ((4-iodobenzyl)oxy)triisopropylsilane to prepare ((4-(3,3-dimethoxypropyl)benzyl)oxy)triisopropylsilane. The structural formula of ((4-(3,3-dimethoxypropyl)benzyl)oxy)triisopropylsilane is shown below:

[0013]

[0014] Step 3: Prepare 4-(3,3-dimethoxypropyl)benzyl alcohol using ((4-(3,3-dimethoxypropyl)benzyl)oxy)triisopropylsilane. The structural formula of 4-(3,3-dimethoxypropyl)benzyl alcohol is as follows:

[0015]

[0016] Step 4: Use 4-(3,3-dimethoxypropyl)benzyl alcohol to prepare 4-(((3-methyl-2-buten-1-yl)oxy)methyl)phenylpropanal dimethyl acetal. The structural formula of 4-(((3-methyl-2-buten-1-yl)oxy)methyl)phenylpropanal dimethyl acetal is as follows:

[0017]

[0018] Step 5: Use 4-(((3-methyl-2-buten-1-yl)oxy)methyl)phenylpropanal dimethyl acetal to prepare 4-(((3-methyl-2-buten-1-yl)oxy)methyl)phenylpropanal to obtain the hyacinth aroma compound.

[0019] Furthermore, in the step 1, the preparation method of (4-iodobenzyl)oxy)triisopropylsilane comprises the following steps:

[0020] A1. Take 4-iodobenzyl alcohol and add it to a dry container. Pour in dichloromethane and stir until it is completely dissolved. Then add imidazole. After cooling to 4-6°C, add triisopropylsilyl chloride dropwise and react at room temperature.

[0021] A2. After the reaction is completed, the mixture is washed with sodium dihydrogen phosphate solution, and the organic phase is separated. The organic phase is evaporated to recover the solvent until a solid is precipitated, and the mixture is cooled to -4 to -6 °C to allow the solid to continue to precipitate. The solid is filtered while cold, washed with anhydrous ethanol, and then dried to obtain ((4-iodobenzyl)oxy)triisopropylsilane.

[0022] Furthermore, in step A1, 0.9-1.1 mol of 4-iodobenzyl alcohol is added to a dry three-necked flask, 900-1100 mL of dichloromethane is poured in and stirred until completely dissolved, then 1.8-2.2 mol of imidazole is added, and after cooling to -4 to -6°C, 1.10-1.12 mol of triisopropylsilyl chloride is added dropwise, and the addition is completed within 20-40 minutes, and then the reaction is carried out at room temperature for 90-150 minutes.

[0023] Furthermore, in step A2, after the reaction is completed, the mixture is washed 2-4 times with 1100-1300 mL of 8-12% sodium dihydrogen phosphate solution, and the organic phase is separated. The obtained organic phase is evaporated to recover the solvent until a small amount of solid is precipitated and cooled to -4 to -6°C. A large amount of solid can be precipitated. The solid is filtered while cold and washed with a small amount of anhydrous ethanol and then dried to obtain a light yellow solid, which is ((4-iodobenzyl)oxy)triisopropylsilane.

[0024] Furthermore, in step 2, the preparation method of ((4-(3,3-dimethoxypropyl)benzyl)oxy)triisopropylsilane comprises the following steps:

[0025] B1. Add ((4-iodobenzyl)oxy)triisopropylsilane to anhydrous ether and stir until completely dissolved to obtain solution A; add magnesium chips and anhydrous ether to a container in a nitrogen atmosphere with a stirring device and a reflux device, then add 1,2-dibromoethane under stirring, and then drop solution A to react to obtain a Grignard reagent;

[0026] B2. Take another container in a nitrogen atmosphere with a stirring device and a reflux device, add anhydrous ether and 1-bromo-3,3-dimethoxypropane, cool to 0°C in an ice-water bath, and then drop the Grignard reagent into it. The temperature should not exceed 10°C during the addition. After the addition is completed, leave it at room temperature to react for 1-5 hours.

[0027] B3. After the reaction is completed, the reaction solution is slowly poured into dilute hydrochloric acid cooled to -4 to -5°C and stirred to quench. During the quenching period, the temperature is kept not higher than 0°C, and the organic phase is separated to obtain an organic phase; the organic phase obtained by separation is washed with sodium bicarbonate solution until it is nearly neutral and then with sodium chloride solution to obtain an organic phase; the organic phase obtained by separation is rotary evaporated and cooled to precipitate a solid, which is filtered while cold and washed with anhydrous ethanol and then dried to obtain ((4-(3,3-dimethoxypropyl)benzyl)oxy)triisopropylsilane.

[0028] Furthermore, in the step B1, 0.8-1.0 mol of ((4-iodobenzyl)oxy)triisopropylsilane is added to 900-1100 mL of anhydrous ether and stirred until completely dissolved to obtain solution A for standby use; 0.9-1.0 mol of magnesium chips and 180-220 mL of anhydrous ether are added to a dry four-necked flask in a nitrogen atmosphere equipped with a thermometer, a stirring device and a reflux device, and the surface oxide layer of the magnesium chips is removed in advance; then 1,2-dibromoethane is added under stirring, the four-necked flask is heated in a water bath, solution A is added dropwise to initiate a reaction, the water bath is removed, solution A is continued to be added dropwise, and the dropping speed is based on the slight reflux of ether; after the dropping is completed, the reaction is continued for 1-5 hours to obtain a Grignard reagent.

[0029] Furthermore, in step B2, a 3000 mL four-necked flask equipped with a thermometer, a stirring device and a reflux device is taken in a dry nitrogen atmosphere, 280-320 mL of anhydrous ether and 0.9-1.0 mol of 1-bromo-3,3-dimethoxypropane are added thereto, and after cooling to 0° C. in an ice-water bath, the Grignard reagent is dripped therein, during which the temperature does not exceed 10° C., and after the dripping is completed, it is placed at room temperature for reaction. After the dripping is completed, it is placed at room temperature for reaction for 1-5 hours.

[0030] Furthermore, in step B3, after the reaction is completed, the reaction solution is slowly poured into 2-4% dilute hydrochloric acid cooled to -4 to -5°C and stirred to quench, and the temperature is kept not higher than 0°C during quenching; the organic phase obtained by separation is washed with 4-6% sodium bicarbonate solution until it is nearly neutral and then washed once with 900-1100mL 9-11% sodium chloride solution, and the organic phase is separated, and the obtained organic phase is rotary evaporated to recover the solvent until a small amount of solid is precipitated and cooled to -5°C, a large amount of solid can be precipitated, and the solid is filtered while cold and washed with a small amount of anhydrous ethanol and then dried to obtain a light yellow solid, that is, ((4-(3,3-dimethoxypropyl)benzyl)oxy)triisopropylsilane.

[0031] Furthermore, in step 3, the preparation method of 4-(3,3-dimethoxypropyl)benzyl alcohol comprises the following steps:

[0032] C1. Take ((4-(3,3-dimethoxypropyl)benzyl)oxy)triisopropylsilane and add it to a container. Pour tetrahydrofuran and stir until it is completely dissolved. Then, drop a tetrahydrofuran solution containing tetrabutylammonium fluoride. After the drop is complete, continue the reaction at room temperature for 50-80 minutes.

[0033] C2. After the reaction is completed, the solvent is recovered by rotary evaporation, cyclohexane and sodium chloride solution are added in sequence and stirred, and then separated to obtain an organic phase 1 and an aqueous phase. The aqueous phase is extracted with cyclohexane to obtain an organic phase 2. The organic phase 1 and the organic phase 2 are combined to obtain an organic phase 3. The organic phase 3 is washed with sodium chloride solution and then separated to obtain an organic phase. The solvent is recovered by rotary evaporation and then distilled under reduced pressure. The fraction at a pressure of 200 Pa and an air temperature of 130-160° C. is collected to obtain 4-(3,3-dimethoxypropyl)benzyl alcohol.

[0034] Furthermore, in the step C1, ((4-(3,3-dimethoxypropyl)benzyl)oxy)triisopropylsilane 0.65-0.75 mol) is added to a three-necked flask, 900-1100 mL of tetrahydrofuran is poured in and stirred until completely dissolved, and then 900-1100 mL of tetrahydrofuran solution containing 0.7-0.8 mol of tetrabutylammonium fluoride is added dropwise. After the addition is complete, the reaction is continued at room temperature for 50-80 min.

[0035] Furthermore, in step C2, after the reaction is completed, the solvent is recovered by rotary evaporation, 900-1100 mL of cyclohexane and 1400-1500 mL of 9-11% sodium chloride solution are added in sequence and stirred for 20-40 min, followed by separation to obtain an organic phase 1 and an aqueous phase, the aqueous phase is extracted 1-3 times with 500-700 mL of cyclohexane to obtain an organic phase 2, and the organic phase 1 and the organic phase 2 are combined to obtain an organic phase 3; the organic phase is washed with 1400-1600 mL of 9-11% sodium chloride solution and then separated to obtain an organic phase, the solvent is recovered by rotary evaporation, and then vacuum distillation is performed, and the fraction at a pressure of 200 Pa and an air temperature of 130-160° C. is collected to obtain a colorless liquid, that is, 4-(3,3-dimethoxypropyl)benzyl alcohol.

[0036] Furthermore, in the step 4, the preparation method of 4-(((3-methyl-2-butene-1-yl)oxy)methyl)phenylpropanal dimethyl acetal comprises the following steps:

[0037] D1. Add tetrahydrofuran to a container, add sodium hydride under stirring, keep stirring in a water bath at room temperature, dropwise add a tetrahydrofuran solution containing 4-(3,3-dimethoxypropyl)benzyl alcohol, and after the dropwise addition, continue the reaction at room temperature for 90-150 minutes;

[0038] D2. 1-chloro-3-methyl-2-butene was added to the obtained reaction solution, and the mixture was refluxed for 12-72 hours and then cooled to room temperature. The reaction solution was poured into an ice-water mixture for quenching. After no more bubbles were generated, cyclohexane was added for stirring and then allowed to stand for separation to obtain an organic phase 1 and an aqueous phase. The aqueous phase was extracted with cyclohexane and separated to obtain an organic phase 2. The organic phase 1 and the organic phase 2 were combined, and the organic phase was washed with sodium chloride solution and separated to obtain an organic phase. The solvent was recovered by rotary evaporation and then distilled under reduced pressure. The fractions at a pressure of 200 Pa and an air temperature of 170-190° C. were collected to obtain 4-(((3-methyl-2-butene-1-yl)oxy)methyl)phenylpropanal dimethyl acetal.

[0039] Furthermore, in the step D1, 250-350 mL of tetrahydrofuran is added to a three-necked flask, and 0.9-1.1 mol of sodium hydride is slowly added under stirring, wherein the sodium hydride is pre-mixed with mineral oil, and the content of sodium hydride in the mixed solution of sodium hydride and mineral oil is 55-65%. After stirring in a water bath at room temperature for 25-35 minutes, 280-320 mL of a tetrahydrofuran solution containing 0.45-0.55 mol of 4-(3,3-dimethoxypropyl)benzyl alcohol is added dropwise, and the addition is completed within 20-40 minutes. After the addition is completed, the reaction is continued at room temperature for 90-150 minutes.

[0040] Further, in step D2, 0.9-1.0 mol of 1-chloro-3-methyl-2-butene is added to the obtained reaction solution, and the mixture is refluxed for 12-72 hours and then cooled to room temperature. The reaction solution is slowly poured into an ice-water mixture for quenching, and after no more bubbles are generated, 900-1100 mL of cyclohexane is added and stirred for 20-40 minutes, and then the mixture is allowed to stand for separation to obtain an organic phase and an aqueous phase, and the aqueous phase is extracted 1-3 times with 900-1100 mL of cyclohexane. The organic phase 2 is obtained by separation, and the organic phase 1 and the organic phase 2 are combined to obtain an organic phase 3; the organic phase 3 is washed with 1700-2100 mL of 9-11% sodium chloride solution and then separated to obtain an organic phase, the solvent is recovered by rotary evaporation and then vacuum distillation is performed, and the fractions at a pressure of 200 Pa and an air temperature of 170-190° C. are collected to obtain a colorless liquid, that is, 4-(((3-methyl-2-butene-1-yl)oxy)methyl)phenylpropanaldehyde dimethyl acetal is obtained.

[0041] Furthermore, in the step 5, the preparation method of 4-(((3-methyl-2-butene-1-yl)oxy)methyl)phenylpropanal comprises the following steps:

[0042] E1. Take 4-(((3-methyl-2-butene-1-yl)oxy)methyl)phenylpropanal dimethyl acetal and add it to a container. Add tetrahydrofuran and dilute hydrochloric acid in sequence under stirring, heat to reflux, and react for 2-6 hours;

[0043] E2. After the reaction is completed, the temperature is cooled to room temperature, and the organic phase is obtained by extraction with cyclohexane. The material is washed with sodium bicarbonate solution until it is nearly neutral and then with sodium chloride solution. The solvent is recovered by rotary evaporation and then vacuum distillation is performed. The fractions at a pressure of 200 Pa and an air temperature of 140-170°C are collected to obtain 4-(((3-methyl-2-butene-1-yl)oxy)methyl)phenylpropanal.

[0044] Furthermore, in step E1, 0.25-0.35 mol of 4-(((3-methyl-2-butene-1-yl)oxy)methyl)phenylpropanaldehyde dimethyl acetal is added to a container, and 280-32 mL of tetrahydrofuran and 550-650 mL of dilute hydrochloric acid are added in sequence under stirring, heated to reflux, and reacted for 3.5-4.5 hours.

[0045] Furthermore, in the step E2, after the reaction is completed, the temperature is cooled to room temperature, and the organic phase is extracted 1-3 times with 1800-2200 mL of cyclohexane to obtain an organic phase, and the material is washed with 4-6% sodium bicarbonate solution until it is nearly neutral and then washed once with 9-11% sodium chloride solution, and then the solvent is recovered by rotary evaporation and then vacuum distillation is performed, and the fractions at a pressure of 200 Pa and an air temperature of 140-170° C. are collected to obtain a colorless liquid, that is, 4-(((3-methyl-2-butene-1-yl)oxy)methyl)phenylpropanal.

[0046] Another object of the present invention is achieved by the following technical scheme: a hyacinth-scented fragrance base, comprising the following raw materials in parts by weight: 160-200 parts of 4-(((3-methyl-2-butene-1-yl)oxy)methyl)phenylpropanal, 40-60 parts of phenylethyl alcohol, 25-35 parts of phenylpropanol, 130-150 parts of cinnamyl alcohol, 40-60 parts of phenylacetaldehyde, 130-170 parts of phenylacetaldehyde dicinnamic acetal, 70-90 parts of hydroxycitronellal, 40-60 parts of methyl ionone, 15-25 parts of ylang-ylang oil, 70-90 parts of 2-phenylethyl isopropyl ether, 70-90 parts of 2-(1-ethoxyethoxy)ethylbenzene, 25-35 parts of benzyl acetate, 15-25 parts of ethyl linalool, 15-25 parts of pinealol, 8-12 parts of bromostyrene, 3-7 parts of cynarolate aldehyde, and 3-7 parts of solanum nigrum aldehyde.

[0047] The beneficial effects of the present invention are as follows: the hyacinth aroma compound prepared by the present invention is 4-(((3-methyl-2-butene-1-yl)oxy)methyl)phenylpropanal, which has the significant floral fragrance characteristics of hyacinth, and has the advantages of obvious fragrance, high molecular weight, long fragrance retention time, good stability, etc., and has important and advantageous uses in the field of perfume adjustment, and can be used in daily chemical products such as soaps, detergents, skin care products, air fresheners, and can also be applied to the fragrance of paper, plastics, leather, fabrics, etc. The compound can be used to prepare a fragrance base, and then the fragrance base is prepared into a daily chemical flavor, and can also be directly used as a raw material for preparing a daily chemical flavor. The preparation method of the hyacinth aroma compound has high production efficiency, is easy to control, and is conducive to industrial production.

[0048] The hyacinth-flavored fragrance base prepared by the invention has significant hyacinth flower fragrance characteristics by adding hyacinth fragrance compounds, has obvious fragrance, long fragrance retention time and good stability. BRIEF DESCRIPTION OF THE DRAWINGS

[0049] Figure 1 This is the gas chromatogram of 4-(((3-methyl-2-buten-1-yl)oxy)methyl)phenylpropanal obtained in Example 1. DETAILED DESCRIPTION

[0050] In order to facilitate the understanding of those skilled in the art, the present invention is further described below in conjunction with embodiments and drawings. The contents mentioned in the implementation modes are not intended to limit the present invention.

[0051] In an embodiment of the present invention, a hyacinth aroma compound has the following structural formula:

[0052]

[0053] The hyacinth aroma compound can be named as: 4-(((3-methyl-2-buten-1-yl)oxy)methyl)phenylpropanal.

[0054] In some embodiments of the present invention, a method for preparing a hyacinth aroma compound comprises the following steps:

[0055] Step 1: Use 4-iodobenzyl alcohol to prepare ((4-iodobenzyl)oxy)triisopropylsilane. The structural formula of ((4-iodobenzyl)oxy)triisopropylsilane is shown below:

[0056]

[0057] Step 2: Use ((4-iodobenzyl)oxy)triisopropylsilane to prepare ((4-(3,3-dimethoxypropyl)benzyl)oxy)triisopropylsilane. The structural formula of ((4-(3,3-dimethoxypropyl)benzyl)oxy)triisopropylsilane is shown below:

[0058]

[0059] Step 3: Prepare 4-(3,3-dimethoxypropyl)benzyl alcohol using ((4-(3,3-dimethoxypropyl)benzyl)oxy)triisopropylsilane. The structural formula of 4-(3,3-dimethoxypropyl)benzyl alcohol is as follows:

[0060]

[0061] Step 4: Use 4-(3,3-dimethoxypropyl)benzyl alcohol to prepare 4-(((3-methyl-2-buten-1-yl)oxy)methyl)phenylpropanal dimethyl acetal. The structural formula of 4-(((3-methyl-2-buten-1-yl)oxy)methyl)phenylpropanal dimethyl acetal is as follows:

[0062]

[0063] Step 5: Use 4-(((3-methyl-2-buten-1-yl)oxy)methyl)phenylpropanal dimethyl acetal to prepare 4-(((3-methyl-2-buten-1-yl)oxy)methyl)phenylpropanal to obtain the hyacinth aroma compound.

[0064] Furthermore, in the step 1, the preparation method of (4-iodobenzyl)oxy)triisopropylsilane comprises the following steps:

[0065] A1. Take 4-iodobenzyl alcohol and add it to a dry container. Pour in dichloromethane and stir until it is completely dissolved. Then add imidazole. After cooling to 4-6°C, add triisopropylsilyl chloride dropwise and react at room temperature.

[0066] A2. After the reaction is completed, the mixture is washed with sodium dihydrogen phosphate solution, and the organic phase is separated. The organic phase is evaporated to recover the solvent until a solid is precipitated, and the mixture is cooled to -4 to -6 °C to allow the solid to continue to precipitate. The solid is filtered while cold, washed with anhydrous ethanol, and then dried to obtain ((4-iodobenzyl)oxy)triisopropylsilane.

[0067] In some embodiments of the present invention, in step A1, 0.9-1.1 mol of 4-iodobenzyl alcohol is added to a dry three-necked flask, 900-1100 mL of dichloromethane is poured in and stirred until completely dissolved, then 1.8-2.2 mol of imidazole is added, and after cooling to -4 to -6°C, 1.10-1.12 mol of triisopropylsilyl chloride is added dropwise, the addition is completed within 20-40 min, and then the reaction is carried out at room temperature for 90-150 min.

[0068] In some embodiments of the present invention, in step A2, after the reaction is completed, the mixture is washed 2-4 times with 1100-1300 mL of 8-12% sodium dihydrogen phosphate solution, and the organic phase is separated. The obtained organic phase is evaporated to recover the solvent until a small amount of solid is precipitated and cooled to -4 to -6°C. A large amount of solid can be precipitated. The solid is filtered while cold and washed with a small amount of anhydrous ethanol and then dried to obtain a light yellow solid, which is ((4-iodobenzyl)oxy)triisopropylsilane.

[0069] In some embodiments of the present invention, in step 2, the method for preparing ((4-(3,3-dimethoxypropyl)benzyl)oxy)triisopropylsilane comprises the following steps:

[0070] B1. Add ((4-iodobenzyl)oxy)triisopropylsilane to anhydrous ether and stir until completely dissolved to obtain solution A; add magnesium chips and anhydrous ether to a container in a nitrogen atmosphere with a stirring device and a reflux device, then add 1,2-dibromoethane under stirring, and then drop solution A to react to obtain a Grignard reagent;

[0071] B2. Take another container in a nitrogen atmosphere with a stirring device and a reflux device, add anhydrous ether and 1-bromo-3,3-dimethoxypropane, cool to 0°C in an ice-water bath, and then drop the Grignard reagent into it. The temperature should not exceed 10°C during the addition. After the addition is completed, leave it at room temperature to react for 1-5 hours.

[0072] B3. After the reaction is completed, the reaction solution is slowly poured into dilute hydrochloric acid cooled to -4 to -5°C and stirred to quench. During the quenching period, the temperature is kept not higher than 0°C, and the organic phase is separated to obtain an organic phase; the organic phase obtained by separation is washed with sodium bicarbonate solution until it is nearly neutral and then with sodium chloride solution to obtain an organic phase; the organic phase obtained by separation is rotary evaporated and cooled to precipitate a solid, which is filtered while cold and washed with anhydrous ethanol and then dried to obtain ((4-(3,3-dimethoxypropyl)benzyl)oxy)triisopropylsilane.

[0073] In some embodiments of the present invention, in the step B1, 0.8-1.0 mol of ((4-iodobenzyl)oxy)triisopropylsilane is added to 900-1100 mL of anhydrous ether and stirred until completely dissolved to obtain solution A for standby use; 0.9-1.0 mol of magnesium chips and 180-220 mL of anhydrous ether are added to a dry four-necked flask in a nitrogen atmosphere equipped with a thermometer, a stirring device and a reflux device, and the surface oxide layer of the magnesium chips is removed in advance; then 1,2-dibromoethane is added under stirring, the four-necked flask is heated in a water bath, solution A is added dropwise to initiate a reaction, the water bath is removed, and solution A is continued to be added dropwise, and the dropping speed is based on the slight reflux of ether; after the dropwise addition is completed, the reaction is continued for 1-5 hours to obtain a Grignard reagent.

[0074] In some embodiments of the present invention, in step B2, a 3000 mL four-necked flask equipped with a thermometer, a stirring device and a reflux device is taken in a dry nitrogen atmosphere, 280-320 mL of anhydrous ether and 0.9-1.0 mol of 1-bromo-3,3-dimethoxypropane are added thereto, and after cooling to 0° C. in an ice-water bath, the Grignard reagent is dripped therein, during which the temperature does not exceed 10° C., and after the addition is completed, it is placed at room temperature for reaction. After the addition is completed, it is placed at room temperature for reaction for 1-5 hours.

[0075] In some embodiments of the present invention, in the step B3, after the reaction is completed, the reaction solution is slowly poured into 2-4% dilute hydrochloric acid cooled to -4 to -5°C and stirred to quench, and the temperature is kept not more than 0°C during the quenching; the organic phase obtained by separation is washed with 4-6% sodium bicarbonate solution until it is nearly neutral and then washed once with 900-1100mL 9-11% sodium chloride solution, and the organic phase is separated, and the obtained organic phase is rotary evaporated to recover the solvent until a small amount of solid is precipitated and cooled to -5°C, a large amount of solid can be precipitated, and the solid is filtered while cold and washed with a small amount of anhydrous ethanol and then dried to obtain a light yellow solid, that is, ((4-(3,3-dimethoxypropyl)benzyl)oxy)triisopropylsilane.

[0076] In some embodiments of the present invention, in step 3, the preparation method of 4-(3,3-dimethoxypropyl)benzyl alcohol comprises the following steps:

[0077] C1. Take ((4-(3,3-dimethoxypropyl)benzyl)oxy)triisopropylsilane and add it to a container. Pour tetrahydrofuran and stir until it is completely dissolved. Then, drop a tetrahydrofuran solution containing tetrabutylammonium fluoride. After the drop is complete, continue the reaction at room temperature for 50-80 minutes.

[0078] C2. After the reaction is completed, the solvent is recovered by rotary evaporation, cyclohexane and sodium chloride solution are added in sequence and stirred, and then separated to obtain an organic phase 1 and an aqueous phase. The aqueous phase is extracted with cyclohexane to obtain an organic phase 2. The organic phase 1 and the organic phase 2 are combined to obtain an organic phase 3. The organic phase 3 is washed with sodium chloride solution and then separated to obtain an organic phase. The solvent is recovered by rotary evaporation and then distilled under reduced pressure. The fraction at a pressure of 200 Pa and an air temperature of 130-160° C. is collected to obtain 4-(3,3-dimethoxypropyl)benzyl alcohol.

[0079] In some embodiments of the present invention, in the step C1, ((4-(3,3-dimethoxypropyl)benzyl)oxy)triisopropylsilane 0.65-0.75 mol) is added to a three-necked flask, 900-1100 mL of tetrahydrofuran is poured in and stirred until completely dissolved, and then 900-1100 mL of tetrahydrofuran solution containing 0.7-0.8 mol of tetrabutylammonium fluoride is added dropwise. After the addition is complete, the reaction is continued at room temperature for 50-80 min.

[0080] In some embodiments of the present invention, in step C2, after the reaction is completed, the solvent is recovered by rotary evaporation, 900-1100 mL of cyclohexane and 1400-1500 mL of 9-11% sodium chloride solution are added in sequence and stirred for 20-40 min, followed by separation to obtain an organic phase 1 and an aqueous phase, the aqueous phase is extracted with 500-700 mL of cyclohexane for 1-3 times to obtain an organic phase 2, and the organic phase 1 and the organic phase 2 are combined to obtain an organic phase 3; the organic phase is washed with 1400-1600 mL of 9-11% sodium chloride solution and then separated to obtain an organic phase, the solvent is recovered by rotary evaporation, and then vacuum distillation is performed, and the fraction at a pressure of 200 Pa and an air temperature of 130-160° C. is collected to obtain a colorless liquid, i.e., 4-(3,3-dimethoxypropyl)benzyl alcohol.

[0081] In some embodiments of the present invention, in step 4, the method for preparing 4-(((3-methyl-2-butene-1-yl)oxy)methyl)phenylpropanal dimethyl acetal comprises the following steps:

[0082] D1. Add tetrahydrofuran to a container, add sodium hydride under stirring, keep stirring in a water bath at room temperature, dropwise add a tetrahydrofuran solution containing 4-(3,3-dimethoxypropyl)benzyl alcohol, and after the dropwise addition, continue the reaction at room temperature for 90-150 minutes;

[0083] D2. 1-chloro-3-methyl-2-butene was added to the obtained reaction solution, and the mixture was refluxed for 12-72 hours and then cooled to room temperature. The reaction solution was poured into an ice-water mixture for quenching. After no more bubbles were generated, cyclohexane was added for stirring and then allowed to stand for separation to obtain an organic phase 1 and an aqueous phase. The aqueous phase was extracted with cyclohexane and separated to obtain an organic phase 2. The organic phase 1 and the organic phase 2 were combined, and the organic phase was washed with sodium chloride solution and separated to obtain an organic phase. The solvent was recovered by rotary evaporation and then distilled under reduced pressure. The fractions at a pressure of 200 Pa and an air temperature of 170-190° C. were collected to obtain 4-(((3-methyl-2-butene-1-yl)oxy)methyl)phenylpropanal dimethyl acetal.

[0084] In some embodiments of the present invention, in the step D1, 250-350 mL of tetrahydrofuran is added to a three-necked flask, and 0.9-1.1 mol of sodium hydride is slowly added under stirring, wherein the sodium hydride is pre-mixed with mineral oil, and the content of sodium hydride in the mixed solution of sodium hydride and mineral oil is 55-65%. After stirring in a water bath at room temperature for 25-35 minutes, 280-320 mL of a tetrahydrofuran solution containing 0.45-0.55 mol of 4-(3,3-dimethoxypropyl)benzyl alcohol is added dropwise, and the addition is completed within 20-40 minutes. After the addition is completed, the reaction is continued at room temperature for 90-150 minutes.

[0085] In some embodiments of the present invention, in the step D2, 0.9-1.0 mol of 1-chloro-3-methyl-2-butene is added to the obtained reaction solution, and the mixture is cooled to room temperature after reflux reaction for 12-72 hours. The reaction solution is slowly poured into an ice-water mixture for quenching, and after no more bubbles are generated, 900-1100 mL of cyclohexane is added, stirred for 20-40 minutes, and then allowed to stand for separation to obtain an organic phase 1 and an aqueous phase. The aqueous phase is extracted with 900-1100 mL of cyclohexane for 1-3 times to obtain an organic phase 2. The organic phase 1 and the organic phase 2 are combined to obtain an organic phase 3; the organic phase 3 is extracted with 1700 -2100mL9-11% sodium chloride solution was used for washing, and then the organic phase was separated. The solvent was recovered by rotary evaporation and then vacuum distillation was performed. The fractions at a pressure of 200Pa and an air temperature of 170-190°C were collected to obtain a colorless liquid, namely 4-(((3-methyl-2-butene-1-yl)oxy)methyl)phenylpropanaldehyde dimethyl acetal.

[0086] In some embodiments of the present invention, in step 5, the method for preparing 4-(((3-methyl-2-butene-1-yl)oxy)methyl)phenylpropanal comprises the following steps:

[0087] E1. Take 4-(((3-methyl-2-butene-1-yl)oxy)methyl)phenylpropanal dimethyl acetal and add it to a container. Add tetrahydrofuran and dilute hydrochloric acid in sequence under stirring, heat to reflux, and react for 2-6 hours;

[0088] E2. After the reaction is completed, the temperature is cooled to room temperature, and the organic phase is obtained by extraction with cyclohexane. The material is washed with sodium bicarbonate solution until it is nearly neutral and then with sodium chloride solution. The solvent is recovered by rotary evaporation and then vacuum distillation is performed. The fractions at a pressure of 200 Pa and an air temperature of 140-170°C are collected to obtain 4-(((3-methyl-2-butene-1-yl)oxy)methyl)phenylpropanal.

[0089] In some embodiments of the present invention, in step E1, 0.25-0.35 mol of 4-(((3-methyl-2-buten-1-yl)oxy)methyl)phenylpropanaldehyde dimethyl acetal is added to a container, and 280-32 mL of tetrahydrofuran and 550-650 mL of dilute hydrochloric acid are added in sequence under stirring, heated to reflux, and reacted for 3.5-4.5 hours.

[0090] In some embodiments of the present invention, in step E2, after the reaction is completed, the temperature is cooled to room temperature, and the organic phase is extracted 1-3 times with 1800-2200 mL of cyclohexane to obtain an organic phase, and the material is washed with 4-6% sodium bicarbonate solution until it is nearly neutral and then washed once with 9-11% sodium chloride solution, and then the solvent is recovered by rotary evaporation and then reduced pressure distillation is performed, and the fractions at a pressure of 200 Pa and an air temperature of 140-170° C. are collected to obtain a colorless liquid, that is, 4-(((3-methyl-2-butene-1-yl)oxy)methyl)phenylpropanal.

[0091] In some embodiments of the present invention, a hyacinth-scented fragrance base comprises the following raw materials in parts by weight: 160-200 parts of 4-(((3-methyl-2-buten-1-yl)oxy)methyl)phenylpropanal, 40-60 parts of phenylethyl alcohol, 25-35 parts of phenylpropanol, 130-150 parts of cinnamyl alcohol, 40-60 parts of phenylacetaldehyde, 130-170 parts of phenylacetaldehyde dicinnamic acetal, 70-90 parts of hydroxycitronellal, 40-60 parts of methyl ionone, 15-25 parts of ylang-ylang oil, 70-90 parts of 2-phenylethyl isopropyl ether, 70-90 parts of 2-(1-ethoxyethoxy)ethylbenzene, 25-35 parts of benzyl acetate, 15-25 parts of ethyl linalool, 15-25 parts of pinealol, 8-12 parts of bromostyrene, 3-7 parts of cynarolic acid aldehyde, and 3-7 parts of solanum nigrum aldehyde.

[0092] Example 1

[0093] This embodiment provides a hyacinth aroma compound having the following structural formula:

[0094]

[0095] The chemical name of the hyacinth aroma compound is: 4-(((3-methyl-2-butene-1-yl)oxy)methyl)phenylpropanal.

[0096] The preparation method of the hyacinth aroma compound comprises the following steps:

[0097] Step 1: Use 4-iodobenzyl alcohol to prepare ((4-iodobenzyl)oxy)triisopropylsilane, the chemical reaction formula is as follows:

[0098]

[0099] A1. Take 4-iodobenzyl alcohol (234.0 g, 1.00 mol) and add it to a dry 2000 mL three-necked flask. Pour dichloromethane (1000 mL) and stir until completely dissolved. Then add imidazole (136.2 g, 2.00 mol). After cooling to 5 °C, add triisopropylsilyl chloride (212.1 g, 1.10 mol) dropwise. The addition is completed over 30 min, and then react at room temperature for 2 h.

[0100] A2. After the reaction is completed, wash with 1200 mL of 10% sodium dihydrogen phosphate solution for 3 times, separate the liquids to obtain the organic phase, and evaporate the obtained organic phase to recover the solvent until a small amount of solid is precipitated. Cool to -5°C, and a large amount of solid can be precipitated. Filter while cold and wash with a small amount of anhydrous ethanol, then dry to obtain 365.5 g of light yellow solid, which is ((4-iodobenzyl)oxy)triisopropylsilane.

[0101] Step 2: Use ((4-iodobenzyl)oxy)triisopropylsilane to prepare ((4-(3,3-dimethoxypropyl)benzyl)oxy)triisopropylsilane, the chemical reaction formula is as follows:

[0102]

[0103] B1. Take ((4-iodobenzyl)oxy)triisopropylsilane (351.0g, 0.90mol) and add it to anhydrous ether (1000mL). Stir until it is completely dissolved to obtain a solution for later use. Add dry magnesium chips (22.8g, 0.95mol) and anhydrous ether (200mL) with the surface oxide layer removed to a 2000mL four-necked flask in a dry nitrogen atmosphere equipped with a thermometer, a stirring device and a reflux device, then add 2-3 drops of 1,2-dibromoethane under rapid stirring, heat the flask slightly in a water bath, slowly drip the above solution to initiate the reaction, remove the water bath, and continue to drip the solution. The dripping speed is based on the slight reflux of the ether. After the dripping is completed, continue the reaction for 3h to obtain the Grignard reagent;

[0104] B2. Take another dry 3000mL four-necked flask in a nitrogen atmosphere equipped with a thermometer, a stirring device and a reflux device, add anhydrous ether (300mL) and 1-bromo-3,3-dimethoxypropane (170.2g, 0.93mol) into it, cool it to 0°C in an ice-water bath, and then drop the Grignard reagent into it. The temperature does not exceed 10°C during the period. After the addition is completed, leave it at room temperature to react for 4h;

[0105] B3. After the reaction is completed, the reaction solution is slowly poured into 3% dilute hydrochloric acid cooled to -5°C and stirred to quench. During the quenching, the temperature is kept not higher than 0°C; the organic phase obtained by separation is washed with 5% sodium bicarbonate solution until it is nearly neutral, and then washed once with 1000mL 10% sodium chloride solution, and the organic phase is separated. The organic phase is evaporated to recover the solvent until a small amount of solid is precipitated, and then cooled to -5°C. A large amount of solid can be precipitated. It is filtered while cold and washed with a small amount of anhydrous ethanol and then dried to obtain 268.9g of light yellow solid, which is ((4-(3,3-dimethoxypropyl)benzyl)oxy)triisopropylsilane.

[0106] Step 3: Use ((4-(3,3-dimethoxypropyl)benzyl)oxy)triisopropylsilane to prepare 4-(3,3-dimethoxypropyl)benzyl alcohol, the chemical reaction formula is as follows:

[0107]

[0108] C1. Take ((4-(3,3-dimethoxypropyl)benzyl)oxy)triisopropylsilane (256.2 g, 0.70 mol) and add it to a 3000 mL three-necked flask. Pour tetrahydrofuran (1000 mL) and stir until it is completely dissolved. Then, drop a tetrahydrofuran (1000 mL) solution containing tetrabutylammonium fluoride (201.4 g, 0.77 mol). After the dropwise addition, continue the reaction at room temperature for 1 h.

[0109] C2. After the reaction, the solvent was recovered by rotary evaporation, cyclohexane (1000 mL) and 10% sodium chloride solution (1500 mL) were added in sequence and stirred for 30 min, followed by separation to obtain an organic phase 1 and an aqueous phase. The aqueous phase was extracted with 600 mL of cyclohexane twice to obtain an organic phase 2. The organic phase 1 and the organic phase 2 were combined to obtain an organic phase 3. The organic phase 3 was washed once with 1500 mL of 10% sodium chloride solution and then separated to obtain an organic phase. The solvent was recovered by rotary evaporation and then vacuum distillation was performed. The fractions at a pressure of 200 Pa and an air temperature of 130-160° C. were collected to obtain 111.4 g of a colorless liquid, which was 4-(3,3-dimethoxypropyl)benzyl alcohol.

[0110] Step 4: Use 4-(3,3-dimethoxypropyl)benzyl alcohol to prepare 4-(((3-methyl-2-butene-1-yl)oxy)methyl)phenylpropanal dimethyl acetal, the chemical reaction formula is as follows:

[0111]

[0112] D1. Take tetrahydrofuran (300 mL) and add it into a 2000 mL three-necked flask. Slowly add sodium hydride (24.0 g, 1.00 mol) under stirring (Note: the reagent used is a mixture of sodium hydride and mineral oil, and the sodium hydride content is 60%, so the actual amount of the reagent added is 40.0 g). Keep stirring in a water bath at room temperature for 30 minutes, then drop a tetrahydrofuran (300 mL) solution containing 4-(3,3-dimethoxypropyl)benzyl alcohol (105.0 g, 0.50 mol) and add the solution dropwise within 30 minutes. After the addition is completed, continue the reaction at room temperature for 2 hours.

[0113] D2, to the obtained reaction solution, add 1-chloro-3-methyl-2-butene (99.4g, 0.95mol), reflux reaction for 50h and then cool to room temperature, slowly pour the reaction solution into an ice-water mixture to quench, add 1000mL of cyclohexane after no longer generating bubbles, stir for 30min and then stand for separation to obtain an organic phase 1 and an aqueous phase, extract the aqueous phase with 1000mL of cyclohexane twice to obtain an organic phase 2, combine the above organic phase 1 and organic phase 2 to obtain an organic phase 3; wash the organic phase 3 once with 2000mL of 10% sodium chloride solution and then separate the liquid to obtain an organic phase, revolve to recover the solvent and then perform reduced pressure distillation, collect the fractions at a pressure of 200Pa and an air temperature of 170-190°C to obtain 94.9g of a colorless liquid, which is 4-(((3-methyl-2-butene-1-yl)oxy)methyl)phenylpropanal dimethyl acetal.

[0114] Step 5: Prepare 4-(((3-methyl-2-buten-1-yl)oxy)methyl)benzylpropanal from 4-(((3-methyl-2-buten-1-yl)oxy)methyl)benzylpropanal dimethyl acetal, the chemical reaction formula is as follows:

[0115]

[0116] E1. Take 4-(((3-methyl-2-butene-1-yl)oxy)methyl)phenylpropanal dimethyl acetal (83.4 g, 0.30 mol) and add it into a 2000 mL three-necked flask. Add tetrahydrofuran (300 mL) and 3% dilute hydrochloric acid (600 mL) in sequence under stirring, heat to reflux, and react for 4 h.

[0117] E2. After the reaction, the mixture was cooled to room temperature, and the organic phase was extracted twice with 2000 mL of cyclohexane to obtain the organic phase. The material was washed with 5% sodium bicarbonate solution until it was nearly neutral, and then washed once with 10% sodium chloride solution. The solvent was then recovered by rotary evaporation and then vacuum distillation was performed. The fractions at a pressure of 200 Pa and an air temperature of 140-170°C were collected to obtain 57.8 g of colorless liquid, which was 4-(((3-methyl-2-butene-1-yl)oxy)methyl)phenylpropanal, with a GC content of 98.5%.

[0118] The 4-(((3-methyl-2-butene-1-yl)oxy)methyl)phenylpropanal prepared in this example has the following NMR spectral characteristics:

[0119] 1H NMR (400MHz, CDCl3) δ9.62(t,J=2.3Hz,1H),7.05(d,J=7.4Hz,2H),6.95(d,J=7.4Hz,2H),5.44( m,1H),4.79(s,2H),4.18(d,J=3.2Hz,2H),2.85(m,2H),2.76(m,2H),1.80(s,3H),1.71(s,3H);

[0120] 13C NMR (100MHz, CDCl3) δ205.0,137.6,138.7,137.5,130.2,128.9,126.0,123.5,116.4,72.9,65.9,44.3,27.0,24.4,18.9.

[0121] The mass spectrometry data are as follows:

[0122] MS (ESI, m / z) 255.1 (M+Na + ); The theoretical calculation data of high-resolution electrospray ionization mass spectrometry is [C 15 H 20 NaO2] + (M+Na + )255.1361, the actual measured value is 255.1358.

[0123] Example 2

[0124] In the present embodiment, a hyacinth-scented fragrance base includes the following raw materials in parts by weight: 180 parts of 4-(((3-methyl-2-butene-1-yl)oxy)methyl)phenylpropanal, 50 parts of phenylethyl alcohol, 30 parts of phenylpropanol, 140 parts of cinnamyl alcohol, 50 parts of phenylacetaldehyde, 150 parts of phenylacetaldehyde dicinnamic acetal, 80 parts of hydroxycitronellal, 50 parts of methyl ionone, 20 parts of ylang-ylang oil, 80 parts of 2-phenylethyl isopropyl ether, 80 parts of 2-(1-ethoxyethoxy)ethylbenzene, 30 parts of benzyl acetate, 20 parts of ethyl linalool, 20 parts of pine alcohol, 10 parts of bromostyrene, 5 parts of cynarolic acid aldehyde, and 5 parts of solanum nigrum aldehyde.

[0125] The hyacinth fragrance base can be prepared by the following steps: adding the compounds described in Table 1 to a reaction device in order according to weight parts, stirring for 1 hour after the addition is completed, to obtain the hyacinth fragrance base; the formula of the hyacinth fragrance base is shown in Table 1 below:

[0126] Table 1 Hyacinth fragrance base formula

[0127] Serial number Raw material name Weight 1 4-(((3-methyl-2-buten-1-yl)oxy)methyl)phenylpropanal 180 2 Phenylethyl alcohol 50 3 Phenylpropanol 30 4 Cinnamyl alcohol 140 5 Phenylacetaldehyde 50 6 Phenylacetaldehyde dicinnamic acetal 150 7 Hydroxycitronellal 80 8 Methyl ionone 50 9 Ylang ylang oil 20 10 2-Phenethyl isopropyl ether 80 11 2-(1-ethoxyethoxy)ethylbenzene 80 12 Benzyl acetate 30 13 Ethyl linalool 20 14 Terpineol 20 15 Bromostyrene 10 16 Cyperus aldehyde 5 17 Solanum nigrum 5 total 1000

[0128] Example 3

[0129] The 4-(((3-methyl-2-butene-1-yl)oxy)methyl)phenylpropanaldehyde prepared in Example 1 was subjected to aroma rating, fragrance retention test and fragrance base aroma test. The test results are as follows:

[0130] (1) Aroma evaluation:

[0131] Thirteen perfumers with more than five years of work experience gave the following evaluations on the aroma of the compound: 13 perfumers believed that the compound had a floral scent, 12 perfumers believed that the compound had a characteristic hyacinth scent, 9 perfumers believed that the compound had a honey-sweet scent, and 7 perfumers believed that the compound had a green scent.

[0132] (2) Fragrance test:

[0133] Take a scent test paper and dip it in 0.5g of 4-(((3-methyl-2-butene-1-yl)oxy)methyl)phenylpropanal. Place the test paper on a scent rack and have 10 perfumers smell it every 4 hours. When more than 2 perfumers cannot perceive the scent of the scent test paper, record the fragrance retention time.

[0134] The fragrance test shows that the fragrance retention time of 4-(((3-methyl-2-butene-1-yl)oxy)methyl)phenylpropanaldehyde is 172 hours. The hyacinth fragrance base has a significant hyacinth flower fragrance characteristic by adding hyacinth fragrance compounds, with obvious fragrance and long fragrance retention time.

[0135] The above embodiments are preferred implementation schemes of the present invention. In addition, the present invention may also be implemented in other ways. Any obvious replacement without departing from the concept of the present invention is within the protection scope of the present invention.

Claims

1. A hyacinth aroma compound, characterized in that: It has the following structural formula:

2. A method for preparing the hyacinth aroma compound according to claim 1, characterized in that: The steps include: Step 1: Use 4-iodobenzyl alcohol to prepare ((4-iodobenzyl)oxy)triisopropylsilane. The structural formula of ((4-iodobenzyl)oxy)triisopropylsilane is shown below: Step 2: Use ((4-iodobenzyl)oxy)triisopropylsilane to prepare ((4-(3,3-dimethoxypropyl)benzyl)oxy)triisopropylsilane. The structural formula of ((4-(3,3-dimethoxypropyl)benzyl)oxy)triisopropylsilane is shown below: Step 3: Prepare 4-(3,3-dimethoxypropyl)benzyl alcohol using ((4-(3,3-dimethoxypropyl)benzyl)oxy)triisopropylsilane. The structural formula of 4-(3,3-dimethoxypropyl)benzyl alcohol is as follows: Step 4: Use 4-(3,3-dimethoxypropyl)benzyl alcohol to prepare 4-(((3-methyl-2-buten-1-yl)oxy)methyl)phenylpropanal dimethyl acetal. The structural formula of 4-(((3-methyl-2-buten-1-yl)oxy)methyl)phenylpropanal dimethyl acetal is as follows: Step 5: Use 4-(((3-methyl-2-buten-1-yl)oxy)methyl)phenylpropanal dimethyl acetal to prepare 4-(((3-methyl-2-buten-1-yl)oxy)methyl)phenylpropanal to obtain the hyacinth aroma compound.

3. The method for preparing the hyacinth aroma compound according to claim 2, characterized in that: In the step 1, the preparation method of (4-iodobenzyl)oxy)triisopropylsilane comprises the following steps: A1. Take 4-iodobenzyl alcohol and add it to a dry container. Pour in dichloromethane and stir until it is completely dissolved. Then add imidazole. After cooling to 4-6°C, add triisopropylsilyl chloride dropwise and react at room temperature. A2. After the reaction is completed, the mixture is washed with sodium dihydrogen phosphate solution, and the organic phase is separated. The organic phase is evaporated to recover the solvent until a solid is precipitated, and the mixture is cooled to -4 to -6 °C to allow the solid to continue to precipitate. The solid is filtered while cold, washed with anhydrous ethanol, and then dried to obtain ((4-iodobenzyl)oxy)triisopropylsilane.

4. The method for preparing the hyacinth aroma compound according to claim 2, characterized in that: In the step 2, the preparation method of ((4-(3,3-dimethoxypropyl)benzyl)oxy)triisopropylsilane comprises the following steps: B1. Add ((4-iodobenzyl)oxy)triisopropylsilane to anhydrous ether and stir until completely dissolved to obtain solution A; add magnesium chips and anhydrous ether to a container in a nitrogen atmosphere with a stirring device and a reflux device, then add 1,2-dibromoethane under stirring, and then drop solution A to react to obtain a Grignard reagent; B2. Take another container in a nitrogen atmosphere with a stirring device and a reflux device, add anhydrous ether and 1-bromo-3,3-dimethoxypropane, cool to 0°C in an ice-water bath, and then drop the Grignard reagent into it. The temperature should not exceed 10°C during the addition. After the addition is completed, leave it at room temperature to react for 1-5 hours. B3. After the reaction is completed, the reaction solution is slowly poured into dilute hydrochloric acid cooled to -4 to -5°C and stirred to quench. During the quenching period, the temperature is kept not higher than 0°C, and the organic phase is separated to obtain an organic phase; the organic phase obtained by separation is washed with sodium bicarbonate solution until it is nearly neutral and then with sodium chloride solution to obtain an organic phase; the organic phase obtained by separation is rotary evaporated and cooled to precipitate a solid, which is filtered while cold and washed with anhydrous ethanol and then dried to obtain ((4-(3,3-dimethoxypropyl)benzyl)oxy)triisopropylsilane.

5. The method for preparing the hyacinth aroma compound according to claim 2, characterized in that: In the step 3, the preparation method of 4-(3,3-dimethoxypropyl)benzyl alcohol comprises the following steps: C1. Take ((4-(3,3-dimethoxypropyl)benzyl)oxy)triisopropylsilane and add it to a container. Pour tetrahydrofuran and stir until it is completely dissolved. Then, drop a tetrahydrofuran solution containing tetrabutylammonium fluoride. After the drop is complete, continue the reaction at room temperature for 50-80 minutes. C2. After the reaction is completed, the solvent is recovered by rotary evaporation, cyclohexane and sodium chloride solution are added in sequence and stirred, and then separated to obtain an organic phase 1 and an aqueous phase. The aqueous phase is extracted with cyclohexane to obtain an organic phase 2. The organic phase 1 and the organic phase 2 are combined to obtain an organic phase 3. The organic phase 3 is washed with sodium chloride solution and then separated to obtain an organic phase. The solvent is recovered by rotary evaporation and then distilled under reduced pressure. The fraction at a pressure of 200 Pa and an air temperature of 130-160° C. is collected to obtain 4-(3,3-dimethoxypropyl)benzyl alcohol.

6. The method for preparing the hyacinth aroma compound according to claim 2, characterized in that: In the step 4, the preparation method of 4-(((3-methyl-2-butene-1-yl)oxy)methyl)phenylpropanaldehyde dimethyl acetal comprises the following steps: D1. Add tetrahydrofuran to a container, add sodium hydride under stirring, keep stirring in a water bath at room temperature, dropwise add a tetrahydrofuran solution containing 4-(3,3-dimethoxypropyl)benzyl alcohol, and after the dropwise addition, continue the reaction at room temperature for 90-150 minutes; D2. 1-chloro-3-methyl-2-butene was added to the obtained reaction solution, and the mixture was refluxed for 12-72 hours and then cooled to room temperature. The reaction solution was poured into an ice-water mixture for quenching. After no more bubbles were generated, cyclohexane was added for stirring and then allowed to stand for separation to obtain an organic phase 1 and an aqueous phase. The aqueous phase was extracted with cyclohexane and separated to obtain an organic phase 2. The organic phase 1 and the organic phase 2 were combined, and the organic phase was washed with sodium chloride solution and separated to obtain an organic phase. The solvent was recovered by rotary evaporation and then distilled under reduced pressure. The fractions at a pressure of 200 Pa and an air temperature of 170-190° C. were collected to obtain 4-(((3-methyl-2-butene-1-yl)oxy)methyl)phenylpropanal dimethyl acetal.

7. The method for preparing the hyacinth aroma compound according to claim 2, characterized in that: In the step 5, the preparation method of 4-(((3-methyl-2-butene-1-yl)oxy)methyl)phenylpropanal comprises the following steps: E1. Take 4-(((3-methyl-2-butene-1-yl)oxy)methyl)phenylpropanal dimethyl acetal and add it to a container. Add tetrahydrofuran and dilute hydrochloric acid in sequence under stirring, heat to reflux, and react for 2-6 hours; E2. After the reaction is completed, the temperature is cooled to room temperature, and the organic phase is obtained by extraction with cyclohexane. The material is washed with sodium bicarbonate solution until it is nearly neutral and then with sodium chloride solution. The solvent is recovered by rotary evaporation and then vacuum distillation is performed. The fractions at a pressure of 200 Pa and an air temperature of 140-170°C are collected to obtain 4-(((3-methyl-2-butene-1-yl)oxy)methyl)phenylpropanal.

8. The method for preparing the hyacinth aroma compound according to claim 7, characterized in that: In the step E1, 0.25-0.35 mol of 4-(((3-methyl-2-butene-1-yl)oxy)methyl)phenylpropanaldehyde dimethyl acetal is added to a container, and 280-32 mL of tetrahydrofuran and 550-650 mL of dilute hydrochloric acid are added in sequence under stirring, and the mixture is heated to reflux and reacted for 3.5-4.5 hours.

9. The method for preparing the hyacinth aroma compound according to claim 7, characterized in that: In the step E2, after the reaction is completed, the temperature is cooled to room temperature, and 1800-2200 mL of cyclohexane is used for 1-3 times to extract the organic phase, and the material is washed with 4-6% sodium bicarbonate solution until it is nearly neutral and then with 9-11% sodium chloride solution, and then the solvent is recovered by rotary evaporation and then reduced pressure distillation is performed, and the fraction at a pressure of 200 Pa and an air temperature of 140-170° C. is collected to obtain 4-(((3-methyl-2-butene-1-yl)oxy)methyl)phenylpropanal.

10. A hyacinth-scented fragrance base, characterized in that: The invention comprises the following raw materials in parts by weight: 160-200 parts of 4-(((3-methyl-2-butene-1-yl)oxy)methyl)phenylpropanal, 40-60 parts of phenylethyl alcohol, 25-35 parts of phenylpropanol, 130-150 parts of cinnamyl alcohol, 40-60 parts of phenylacetaldehyde, 130-170 parts of phenylacetaldehyde dicinnamic acetal, 70-90 parts of hydroxycitronellal, 40-60 parts of methyl ionone, 15-25 parts of ylang-ylang oil, 70-90 parts of 2-phenylethyl isopropyl ether, 70-90 parts of 2-(1-ethoxyethoxy)ethylbenzene, 25-35 parts of benzyl acetate, 15-25 parts of ethyl linalool, 15-25 parts of pinealol, 8-12 parts of bromostyrene, 3-7 parts of cynarolate aldehyde and 3-7 parts of solanum nigrum aldehyde.

Images