A method for synthesizing cyclohexane dicarboxylic acid monoester compounds

Abstract

The application belongs to the technical field of organic synthesis, and particularly relates to a synthesis method of cyclohexane dicarboxylic acid monoester compounds. The method comprises the following steps: 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride is used as a water reducing agent, 4-dimethylaminopyridine (DMAP) is used as a catalyst, a compound of formula (1) is mixed with a compound of formula (2) to obtain the cyclohexane dicarboxylic acid monoester compounds. The raw materials and catalysts used in the application are cheap and easy to obtain, the reaction operation is simple, the synthesis route is simplified, the reaction condition is mild, and no toxic compound is involved. By adjusting the ratio of the compound of formula (2) to the water reducing agent and the water content of the water reducing agent, the double-substituted impurities can be effectively controlled, and the generation rate of the cyclohexane dicarboxylic acid monoester compounds is improved.

Description

Technical Field

[0001] This invention belongs to the field of organic synthesis technology, specifically relating to a method for synthesizing cyclohexane dicarboxylic acid monoester compounds. Background Technology

[0002] Cyclohexanedicarboxylic acid monoesters are frequently used as side chain segments in the formation of optically anisotropic liquid crystal compounds, playing a crucial role in the liquid crystal display field. In recent years, their application in electronic chemical materials has also been extensively studied. Currently, the synthesis of cyclohexanedicarboxylic acid monoesters mainly relies on the esterification reaction of hydroxyl compounds with carboxylic acid compounds.

[0003] Patent CN112771020A proposes a method using cyclohexanedicarboxylic acid and 4-((methanesulfonyl)oxy)butyl acrylate as raw materials, reacting them at 90°C for 5 hours under the action of triethylamine and DMAc, followed by extraction with sodium hydroxide solution and water, and separation by column chromatography to obtain cyclohexanedicarboxylic acid monoester. This method involves high reaction temperatures and a high content of the dicarboxylic acid diester byproduct, making post-processing purification relatively troublesome. Patent CN104950373B reacts cyclohexanedicarboxylic acid with methanesulfonyl chloride at room temperature under the action of triethylamine, adding DMAP and 4-hydroxybutyl acrylate to the system, stirring at room temperature for 4 hours, washing with water, and purifying by column chromatography to obtain cyclohexanedicarboxylic acid monoester with a yield of 75%. Although this method has a higher yield, the methanesulfonyl chloride used in the reaction is a highly toxic substance, and its large-scale purchase is limited, making industrial-scale promotion of this method difficult. Patent JP6871418B2 employs a multi-step method to synthesize cyclohexanedicarboxylic acid monoester. First, cyclohexanedicarboxylic acid is converted to an acyl chloride via thionyl chloride under DMF catalysis. Then, it reacts with 4-hydroxybutylvinyl ether in the presence of triethylamine to form a symmetrical vinyl ether structure. Next, an intermediate is prepared by reacting with a base and acid. Finally, it reacts with acryloyl chloride in the presence of N,N-dimethylaniline to obtain methyl cyclohexanedicarboxylic acid. This reaction effectively controls the formation of dicarboxylic acid diester byproducts, but the reaction route is long, requiring five steps to obtain the target compound, resulting in low yield and making industrial-scale production difficult.

[0004] In summary, current methods for synthesizing cyclohexane dicarboxylic acid monoesters suffer from problems such as long reaction routes, complex preparation processes, difficulties in post-processing and purification, the involvement of highly toxic compounds, and low yields. Therefore, providing a simple, fewer-step, and highly purified method for synthesizing cyclohexane dicarboxylic acid monoesters is of great significance for their industrial production. Summary of the Invention

[0005] The purpose of this invention is to provide a method for synthesizing cyclohexane dicarboxylic acid monoester compounds, thereby reducing the difficulty of their industrial production.

[0006] To address this need in the field, this application provides a method for synthesizing cyclohexane dicarboxylic acid monoester compounds.

[0007] On one hand, the present invention relates to a method for synthesizing a cyclohexane dicarboxylic acid monoester compound, comprising: using 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride as a dehydrating agent and 4-dimethylaminopyridine as a catalyst, mixing and reacting the compound shown in formula (1) with the compound shown in formula (2) to obtain a cyclohexane dicarboxylic acid monoester compound, wherein the cyclohexane dicarboxylic acid monoester compound is shown in formula (3);

[0008]

[0009] Where m represents the number of cyclohexyl groups in the structure, m = 1, 2;

[0010] n represents the number of alkyl carbon atoms in the acrylate fragment, n = 2, 3, 4, 6.

[0011] Furthermore, in the method for synthesizing cyclohexane dicarboxylic acid monoester compounds provided by the present invention, the molar ratio of the compound of formula (1), 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride, 4-dimethylaminopyridine, and the compound of formula (2) is 1:0.9-1.1:0.1-0.3:0.7-1.

[0012] Furthermore, in the method for synthesizing cyclohexane dicarboxylic acid monoester compounds provided by the present invention, the water content of the 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride is 1.0 wt% to 3.0 wt%.

[0013] Furthermore, in the method for synthesizing cyclohexane dicarboxylic acid monoester compounds provided by the present invention, the mixing reaction is carried out in a solvent, wherein the solvent is dichloromethane or toluene.

[0014] Furthermore, in the method for synthesizing cyclohexane dicarboxylic acid monoester compounds provided by the present invention, the reaction temperature of the mixed reaction is -10℃ to 25℃, and the reaction time is 1-8h.

[0015] Furthermore, the method for synthesizing cyclohexane dicarboxylic acid monoester compounds provided by the present invention also includes a post-processing procedure, which includes: after the mixing reaction is completed, water is added to the reaction solution, the organic phase is separated after washing with water three times, the organic phase is concentrated under reduced pressure, toluene and water are added to it, the organic phase is separated after washing with water three times, the organic phase is dried, concentrated under reduced pressure and passed through a silica gel column, the column solvent is concentrated to dryness, and recrystallized once with a mixed solvent of toluene and methylcyclohexane to obtain the cyclohexane dicarboxylic acid monoester compounds.

[0016] Preferably, in the method for synthesizing cyclohexane dicarboxylic acid monoester compounds provided by the present invention, m = 1.

[0017] Preferably, in the method for synthesizing cyclohexane dicarboxylic acid monoester compounds provided by the present invention, n = 2 or 4; more preferably, n = 4.

[0018] Compared with the prior art, the present invention has the following beneficial effects or advantages:

[0019] This invention provides a method for synthesizing cyclohexane dicarboxylic acid monoesters, using inexpensive 4-dimethylaminopyridine as a catalyst and 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride as a dehydrating agent, to synthesize the target compound through a one-step esterification reaction. The method for synthesizing cyclohexane dicarboxylic acid monoesters provided by this invention features simple reaction operation, inexpensive raw materials, a simple synthetic route, mild reaction conditions, and the absence of highly toxic compounds. By adjusting the ratio of the compound in formula (2) to the dehydrating agent, and the moisture content of the dehydrating agent, this invention can effectively control disubstituted impurities and improve the yield of cyclohexane dicarboxylic acid monoesters. This invention adjusts the water content of 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride to appropriately weaken its dehydration ability and improve the selectivity of the reaction, thereby directionally promoting the reaction towards the formation of cyclohexane-1,4-dicarboxylic acid monoester. It effectively inhibits the formation of dicarboxylic acid diester, and increases the GC content of dicarboxylic acid monoester compound in the reaction solution to over 80%. Pure product can be obtained through simple post-treatment purification. Attached Figure Description

[0020] Figure 1 The (1R,4R)-4-((4-(acryloyloxy)butoxy)carbonyl)cyclohexane-1-carboxylic acid prepared in Example 1 1 H-NMR spectrum.

[0021] Figure 2 The mass spectrum is that of (1R,4R)-4-((4-(acryloyloxy)butoxy)carbonyl)cyclohexane-1-carboxylic acid prepared in Example 1.

[0022] Figure 3 The infrared spectrum of (1R,4R)-4-((4-(acryloyloxy)butoxy)carbonyl)cyclohexane-1-carboxylic acid prepared in Example 1. Detailed Implementation

[0023] The technical solution of the present invention will be described below with reference to the embodiments. However, the present invention is not limited to the following embodiments.

[0024] To enable those skilled in the art to better understand and implement the technical solutions of the present invention, the present invention will be further described below in conjunction with specific embodiments and accompanying drawings. However, the embodiments described are not intended to limit the present invention.

[0025] Unless otherwise specified, the experimental and detection methods described in the following embodiments are conventional methods; unless otherwise specified, the reagents and materials are commercially available.

[0026] Example 1

[0027] This embodiment provides a preparation experiment for (1R,4R)-4-((4-(acryloyloxy)butoxy)carbonyl)cyclohexane-1-carboxylic acid.

[0028] In this embodiment, m = 1, n = 4, and the water content of the 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDCI) used is 2.0 wt%. The synthetic route used in this embodiment is as follows:

[0029]

[0030] Under nitrogen protection, 100g of trans-1,4-cyclohexanedicarboxylic acid, 21.3g of 4-dimethylaminopyridine (DMAP), and 1500mL of dichloromethane were sequentially added to a 5L three-necked flask. The mixture was stirred and heated to reflux (42℃). After maintaining reflux for 0.5h, the temperature was lowered to 20℃-25℃, and 111.34g of EDCI (containing 2.0wt% water) was added. The mixture was stirred for 10min, and a dichloromethane solution of 4-hydroxybutylacrylate (58.61g of 4-hydroxybutylacrylate dissolved in 1500mL of dichloromethane) was added dropwise at 20℃-25℃. After the addition was complete, the mixture was kept at 20℃-25℃ for 2h. GC analysis showed that the reactants had largely reacted (cyclohexanedicarboxylic acid monoester GC = 81.4%, dicarboxylic acid diester byproduct GC = 13.7%), and the reaction was stopped.

[0031] Add 3000 mL of water to the reaction solution, wash three times with water, and separate the organic phase. Concentrate the organic phase under reduced pressure, add 1600 mL of toluene and 1600 mL of water, wash three times with water, and separate the organic phase. Dry the organic phase with anhydrous magnesium sulfate and concentrate under reduced pressure until 100 mL of toluene remains. Pass the concentrate through a silica gel column, dry the column chromatography solution, and recrystallize once with a mixed solvent of toluene and methylcyclohexane to obtain 72.78 g of white solid, which is (1R,4R)-4-((4-(acryloyloxy)butoxy)carbonyl)cyclohexane-1-carboxylic acid, with a yield of 60% and a GC content of 99.3%.

[0032] Figure 1 It is the (1R,4R)-4-((4-(acryloyloxy)butoxy)carbonyl)cyclohexane-1-carboxylic acid prepared in Example 1.1 The H-NMR spectrum and NMR spectrum data are as follows: 1 HNMR(600MHz,Chloroform-d)δ6.39(dd,J=17.4,1.4Hz,1H),6.13(dd,J=17.3,10.4Hz,1H),5.84(dd,J=10.4,1.4Hz,1H),4.20–4 .18(t,2H),4.11(t,J=6.1Hz,2H),2.36–2.24(m,2H),2.08(m,J=17.6,6.5,5.7,3.1Hz,4H),1.80–1.68(m,4H),1.52–1.41(m,4H).

[0033] Figure 2 The MS (m / z) plot of (1R,4R)-4-((4-(acryloyloxy)butoxy)carbonyl)cyclohexane-1-carboxylic acid prepared in Example 1 is: 370 (m / z + trimethylsilyl), 325, 280, 226, 183, 127, 73.

[0034] Figure 3 This is the infrared spectrum of (1R,4R)-4-((4-(acryloyloxy)butoxy)carbonyl)cyclohexane-1-carboxylic acid prepared in Example 1. Figure 3 It can be seen that the wave number is 3429 cm⁻¹ -1 1770~1700cm -1 1200~1170cm -1 The absorption peaks at 3200–2500 cm⁻¹ correspond to the characteristic peaks of the C=O stretching vibration and CO stretching vibration on the ester group, respectively, indicating that the compound contains an ester group. -1 The broad and diffuse peaks are the stretching vibration peaks of the OH group in the carboxyl group, ranging from 1740 to 1690 cm⁻¹. -1 The presence of a C=O stretching vibration characteristic peak indicates the presence of a carboxyl group in the molecule, with a wavenumber of 3042 cm⁻¹. -1 1635cm -1 The absorption peaks, attributed to the carbon-hydrogen bond and stretching vibration of C=CH respectively, indicate the presence of an alkene bond in the molecule. (2925 cm⁻¹) -1 and 2897cm -1 The characteristic peaks corresponding to the stretching vibrations of CH indicate that the compound contains methylene and methine groups. Infrared spectroscopy analysis shows that the functional groups in the product obtained in Example 1 are consistent with those in the expected product.

[0035] Example 2

[0036] This embodiment provides an experimental preparation of (1R,1'R,4R,4'R)-4'-((4-(acryloyloxy)butoxy)carbonyl)-[1,1'-bis(cyclohexane)]-4-carboxylic acid.

[0037] In this embodiment, m = 2, n = 4, and the water content of the 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDCI) used is 1.5 wt%. The synthetic route used in this embodiment is as follows:

[0038]

[0039] Under nitrogen protection, 100g of (trans,trans)-[1,1'-bicyclohexane]-4,4'-dicarboxylic acid, 14.41g of 4-dimethylaminopyridine (DMAP), and 1500mL of dichloromethane were sequentially added to a 5L three-necked flask. The mixture was stirred and heated to reflux (42℃). After maintaining reflux for 0.5h, the temperature was lowered to 20℃-25℃, and 75.37g of EDCI (1.5wt% water content) was added. The mixture was stirred for 10min, and a dichloromethane solution of 4-hydroxybutylacrylate (39.68g of 4-hydroxybutylacrylate dissolved in 1500mL of dichloromethane) was added dropwise at 20℃-25℃. After the addition was complete, the mixture was kept at 20℃-25℃ for 2h. GC analysis showed that the reactants had largely reacted (cyclohexanedicarboxylic acid monoester GC = 80.7%), and the reaction was stopped.

[0040] Add 3000 mL of water to the reaction solution, wash three times with water, and separate the organic phase. Concentrate the organic phase under reduced pressure, add 1600 mL of toluene and 1600 mL of water, wash three times with water, and separate the organic phase. Dry the organic phase with anhydrous magnesium sulfate and concentrate under reduced pressure until 100 mL of toluene remains. Pass the concentrate through a silica gel column, dry it to dryness, and recrystallize it once with a mixed solvent of toluene and methylcyclohexane to give 58.64 g of white solid, which is (1R,1'R,4R,4'R)-4'-((4-(acryloyloxy)butoxy)carbonyl)-[1,1'-bis(cyclohexane)]-4-carboxylic acid, with a yield of 56% and a GC content of 99.0%.

[0041] Example 3

[0042] This embodiment provides a preparation experiment for (1R,4R)-4-((2-(acryloyloxy)ethoxy)carbonyl)cyclohexane-1-carboxylic acid.

[0043] In this embodiment, m = 1, n = 2, and the water content of the 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDCI) used is 2.5 wt%. The synthetic route used in this embodiment is as follows:

[0044]

[0045] Under nitrogen protection, 100g of trans-1,4-cyclohexanedicarboxylic acid, 21.3g of 4-dimethylaminopyridine (DMAP), and 1500mL of dichloromethane were sequentially added to a 5L three-necked flask. The mixture was stirred and heated to reflux (42℃). After maintaining reflux for 0.5h, the temperature was lowered to 20℃-25℃, and 111.34g of EDCI (containing 2.5wt% water) was added. The mixture was stirred for 10min, and a dichloromethane solution of 2-hydroxyethyl acrylate (47.2g of 2-hydroxyethyl acrylate dissolved in 1500mL of dichloromethane) was added dropwise at 20℃-25℃. After the addition was complete, the mixture was kept at 20℃-25℃ for 2h. GC analysis showed that the reactants had largely reacted (cyclohexanedicarboxylic acid monoester GC = 81.1%), and the reaction was stopped.

[0046] Add 3000 mL of water to the reaction solution, wash three times with water, and separate the organic phase. Concentrate the organic phase under reduced pressure, add 1600 mL of toluene and 1600 mL of water, wash three times with water, and separate the organic phase. Dry the organic phase with anhydrous magnesium sulfate and concentrate under reduced pressure until 100 mL of toluene remains. Pass the concentrate through a silica gel column, dry the column chromatography solution, and recrystallize once with a mixed solvent of toluene and methylcyclohexane to obtain 60.43 g of white solid, which is (1R,4R)-4-((2-(acryloyloxy)ethoxy)carbonyl)cyclohexane-1-carboxylic acid, with a yield of 55% and a GC content of 99.2%.

[0047] Example 4

[0048] This embodiment provides an experimental preparation of (1R,1'R,4R,4'R)-4'-((3-(acryloyloxy)propoxy)carbonyl)-[1,1'-bis(cyclohexane)]-4-carboxylic acid.

[0049] In this embodiment, m = 2, n = 3, and the water content of the 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDCI) used is 2.5 wt%. The reaction equation for this embodiment is as follows:

[0050]

[0051] The specific experimental procedures were the same as those in the above examples. The experimental results were as follows: the main content of cyclohexanedicarboxylic acid monoester in the reaction solution was 80.5% (GC content), and after recrystallization and purification, the main GC content was 99.0%, with a yield of 52%.

[0052] Example 5

[0053] This embodiment provides an experimental preparation of (1R,1'R,4R,4'R)-4'-((6-(acryloyloxy)hexyloxy)carbonyl)-[1,1'-bis(cyclohexane)]-4-carboxylic acid.

[0054] In this embodiment, m = 2, n = 6, and the water content of the 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDCI) used is 2.5 wt%. The reaction equation for this embodiment is as follows:

[0055]

[0056] The specific experimental procedures were the same as in the above examples. The experimental results were as follows: the main content of cyclohexanedicarboxylic acid monoester in the reaction solution was 80.2% (GC), and after recrystallization and purification, the main GC content was 99.2%, with a yield of 50%.

[0057] Comparative Example 1

[0058] This embodiment provides a preparation experiment of the dehydrating agent 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDCI) used in the reaction with a water content of 0.1 wt%.

[0059] In this embodiment, m = 1, n = 4, and the water content of the 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDCI) used is 0.1 wt%. The synthetic route used in this embodiment is as follows:

[0060]

[0061] Under nitrogen protection, 100g of trans-1,4-cyclohexanedicarboxylic acid, 21.3g of 4-dimethylaminopyridine (DMAP), and 1500mL of dichloromethane were sequentially added to a 5L three-necked flask. The mixture was stirred and heated to reflux (42℃). After maintaining reflux for 0.5h, the temperature was lowered to 20℃-25℃, and 111.34g of EDCI (0.1wt% water content) was added. The mixture was stirred for 10min, and a dichloromethane solution of 4-hydroxybutylacrylate (58.61g of 4-hydroxybutylacrylate dissolved in 1500mL of dichloromethane) was added dropwise at 20℃-25℃. After the addition was complete, the mixture was kept at 20℃-25℃ for 2h. GC analysis showed that the reactants had largely reacted (cyclohexanedicarboxylic acid monoester GC = 54.2%, dicarboxylic acid diester byproduct GC = 39.5%). The reaction was then stopped.

[0062] Comparative Example 2

[0063] This embodiment provides a preparation experiment of the dehydrating agent 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDCI) used in the reaction with a water content of 5.0 wt%.

[0064] In this embodiment, m = 1, n = 4, and the water content of the 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDCI) used is 5.0 wt%. The synthetic route used in this embodiment is as follows:

[0065]

[0066] Under nitrogen protection, 100g of trans-1,4-cyclohexanedicarboxylic acid, 21.3g of 4-dimethylaminopyridine (DMAP), and 1500mL of dichloromethane were sequentially added to a 5L three-necked flask. The mixture was stirred and heated to reflux (42℃). After reflux for 0.5h, the temperature was lowered to 20℃-25℃, and 111.34g of EDCI (5.0wt% water content) was added. The mixture was stirred for 10min, and a dichloromethane solution of 4-hydroxybutylacrylate (58.61g of 4-hydroxybutylacrylate dissolved in 1500mL of dichloromethane) was added dropwise at 20℃-25℃. After the addition was complete, the mixture was kept at 20℃-25℃ for 2h. GC analysis showed that a large amount of raw material remained and the reaction could not continue (GC of cyclohexanedicarboxylic acid = 59.4%, GC of cyclohexanedicarboxylic acid monoester = 28.7%). The reaction was then stopped.

[0067] Comparative Examples 1 and 2 show that when the water content in EDCI is low (less than 1.0 wt%), EDCI has a strong dehydration ability, easily removing two molecules of water and promoting the formation of a large amount of dicarboxylic acid ester byproducts. When the water content in EDCI is high (greater than 3.0 wt%), its dehydration ability weakens, its reactivity deteriorates, a large amount of raw material remains, and the conversion rate is low. Therefore, the water content of EDCI should be controlled within the range of 1.0 wt% to 3.0 wt%, so that the raw materials are basically completely reacted, mainly forming the target compound, cyclohexanedicarboxylic acid monoester.

[0068] In summary, this invention proposes that the water content of the dehydrating agent EDCI used in the experiment significantly affects the reaction effect. When the water content of EDCI is low, its dehydrating ability is strong, promoting the formation of a large amount of dicarboxylic acid diester byproducts. When the water content of EDCI is too high, the reactivity deteriorates, resulting in a large amount of raw material residue and incomplete reaction. Therefore, precisely adjusting the water content of EDCI can directionally control the reaction towards the formation of dicarboxylic acid monoester compounds, effectively controlling the generation of dicarboxylic acid diester byproducts.

[0069] As described above, the present invention can be well implemented. The above embodiments are merely descriptions of preferred embodiments of the present invention and are not intended to limit the scope of the present invention. Without departing from the spirit of the present invention, all changes and improvements made by those skilled in the art to the technical solutions of the present invention should fall within the protection scope defined by the present invention.

Claims

1. A method for synthesizing cyclohexane dicarboxylic acid monoester compounds, characterized in that, include: Using 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride as a dehydrating agent and 4-dimethylaminopyridine as a catalyst, the compound shown in formula (1) and the compound shown in formula (2) were mixed and reacted to obtain cyclohexane dicarboxylic acid monoester compounds, which are shown in formula (3). Where m represents the number of cyclohexyl groups in the structure, m=1, 2; n represents the number of alkyl carbon atoms in the acrylate fragment, n = 2, 3, 4, 6; The molar ratio of the compound of formula (1), 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride, 4-dimethylaminopyridine, and the compound of formula (2) is 1:0.9-1.1:0.1-0.3:0.7-1; The water content of the 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride is 1.0 wt% to 3.0 wt%. The reaction temperature of the mixture is -10℃ to 25℃, and the reaction time is 1-8h.

2. The method for synthesizing cyclohexane dicarboxylic acid monoester compounds according to claim 1, characterized in that, The mixing reaction is carried out in a solvent, which is either dichloromethane or toluene.

3. The method for synthesizing cyclohexane dicarboxylic acid monoester compounds according to claim 1, characterized in that, The process also includes a post-processing procedure, which includes: after the mixing reaction is completed, water is added to the reaction solution, the organic phase is separated after washing with water three times, the organic phase is concentrated under reduced pressure, toluene and water are added to it, the organic phase is separated after washing with water three times, the organic phase is dried, concentrated under reduced pressure and passed through a silica gel column, the column liquid is concentrated to dryness, and recrystallized once with a mixed solvent of toluene and methylcyclohexane to obtain the cyclohexane dicarboxylic acid monoester compound.

4. The method for synthesizing cyclohexane dicarboxylic acid monoester compounds according to claim 1, characterized in that, The value of m is 1.

5. The method for synthesizing cyclohexane dicarboxylic acid monoester compounds according to claim 1, characterized in that, The values ​​are n=2 and 4.

6. The method for synthesizing cyclohexane dicarboxylic acid monoester compounds according to claim 5, characterized in that, The n=4.

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