CN116253638A - Method for synthesizing 2, 4-dimethoxy benzoyl chloride and 2, 4-dimethoxy benzoic acid - Google Patents

Method for synthesizing 2, 4-dimethoxy benzoyl chloride and 2, 4-dimethoxy benzoic acid Download PDF

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CN116253638A
CN116253638A CN202310081137.3A CN202310081137A CN116253638A CN 116253638 A CN116253638 A CN 116253638A CN 202310081137 A CN202310081137 A CN 202310081137A CN 116253638 A CN116253638 A CN 116253638A
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dimethoxy
synthesizing
benzoyl chloride
chloride
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杨振宁
陈义文
周家伟
向蓉
彭盛娟
王荣
张元勇
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CHONGQING CHANGFENG CHEMICAL INDUSTRY CO LTD
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/58—Preparation of carboxylic acid halides
    • C07C51/62—Preparation of carboxylic acid halides by reactions not involving the carboxylic acid halide group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/04—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid halides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/42—Separation; Purification; Stabilisation; Use of additives
    • C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/58—Preparation of carboxylic acid halides
    • C07C51/64—Separation; Purification; Stabilisation; Use of additives
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
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Abstract

The invention discloses a method for synthesizing 2, 4-dimethoxy benzoyl chloride, which is characterized by comprising the following steps of: the preparation method comprises the steps of taking m-xylylene ether and oxalyl chloride as raw materials, reacting at 50-80 ℃ in the presence of an organic solvent and a catalyst until the reaction is complete, evaporating the solvent, and then performing reduced pressure distillation to obtain 2, 4-dimethoxy benzoyl chloride, wherein the catalyst is azodiisobutyronitrile or benzoyl peroxide. The method for synthesizing 2, 4-dimethoxy benzoic acid is characterized in that: according to the method of any one of claims 1-5, 2, 4-dimethoxy benzoyl chloride is prepared, water is added for hydrolysis, and then 2, 4-dimethoxy benzoic acid is obtained through recrystallization. The method has the advantages of mild reaction conditions, short synthesis steps, low cost, little pollution to the environment, high yield and good product quality.

Description

Method for synthesizing 2, 4-dimethoxy benzoyl chloride and 2, 4-dimethoxy benzoic acid
Technical Field
The invention relates to a method for synthesizing 2, 4-dimethoxy benzoyl chloride and 2, 4-dimethoxy benzoic acid, belonging to the technical field of organic synthesis.
Background
The 2, 4-dimethoxy benzoic acid is an important chemical intermediate, can be widely used for synthesizing antibacterial synergists, anxiolytics, coronary vasodilators and the like, has been reported in synthetic chemistry, namely synthetic chemistry, cheinese journal of synthetic chemistry, (synthetic chemistry, vol (15,200), no. 6, 789-791), the method takes 2, 4-dihydroxy benzoic acid as a raw material to react with dimethyl sulfate, relates to thionyl chloride, or takes resorcinol as a raw material, firstly reacts with carbon dioxide in the presence of sodium bicarbonate to obtain 2, 4-dihydroxy benzoic acid, then reacts with dimethyl sulfate, and the dimethyl sulfate is a highly toxic substance, and the thionyl chloride has large environmental pollution, long steps, low synthesis yield, complex process and high production cost.
Disclosure of Invention
In view of the above problems, a first object of the present invention is to provide a method for synthesizing 2, 4-dimethoxybenzoyl chloride, and a second object of the present invention is to provide 2, 4-dimethoxybenzoic acid which has simple process steps, mild reaction conditions, little environmental pollution and high yield.
In order to achieve the first object, the technical scheme of the invention is as follows: a method for synthesizing 2, 4-dimethoxy benzoyl chloride, which is characterized by comprising the following steps: the method comprises the steps of taking m-xylylene ether and oxalyl chloride as raw materials, reacting in the presence of an organic solvent and a catalyst until the reaction is complete, and then removing the organic solvent by reduced pressure distillation to obtain 2, 4-dimethoxy benzoyl chloride, wherein the catalyst is azodiisobutyronitrile or benzoyl peroxide. The reaction formula is:
Figure BDA0004067441230000021
in the scheme, the method comprises the following steps: the dosage of the catalyst is 1% -2% of the mass of the m-xylylene ether. The amount of the organic solvent added was about 1ml of the solvent per 1g of m-xylylene ether.
In the scheme, the method comprises the following steps: the catalyst is added in portions.
In the scheme, the method comprises the following steps: the organic solvent is one of toluene, xylene, 1, 2-dichloroethane, carbon tetrachloride, chloroform, dichlorobenzene and petroleum ether.
In the scheme, the method comprises the following steps: the molar ratio of the m-xylylene ether to the oxalyl chloride is 1:1-1:1.2.
In the scheme, the method comprises the following steps: the operation steps are as follows: adding m-xylylene ether into a reaction vessel, stirring, adding part of catalyst, heating to 50-60 ℃, dropwise adding a mixed solution of oxalyl chloride and an organic solvent, controlling the temperature to react at 70-90 ℃ after the dropwise adding, adding the rest catalyst in batches in the process of dropwise adding oxalyl chloride and the reaction, and removing the organic solvent by reduced pressure distillation after the reaction is completed to obtain the 2, 4-dimethoxy benzoyl chloride.
The second object of the present invention is achieved by: a method for synthesizing 2, 4-dimethoxy benzoic acid is characterized in that: according to the method, the 2, 4-dimethoxy benzoyl chloride is prepared, water is added for hydrolysis, and then the 2, 4-dimethoxy benzoic acid is obtained through recrystallization.
In the scheme, the method comprises the following steps: the solvent used for recrystallization is water.
Compared with the prior art, the invention has the beneficial effects that: the method does not need dimethyl sulfate, does not exist sulfoxide chloride, has little environmental pollution, has simple reaction operation by taking the m-xylylene ether and oxalyl chloride as raw materials, has short synthesis steps and low cost, has the yield of the 2, 4-dimethoxy benzoic acid of more than 95 percent and the purity of more than 99.5 percent, and can be widely used in the fields of chemical industry, pharmacy and the like.
Detailed Description
The invention is further illustrated by the following examples:
in example 1, 13.8g of m-xylylene ether is put into a three-neck flask, 0.05g of azobisisobutyronitrile is added, the magnetic stirrer is put into the flask and is started to stir, when the temperature is raised to 50 ℃ as indicated by heating, the solution consisting of 12.8g of oxalyl chloride and 15ml of chlorobenzene is started to be dripped for 15 minutes, the dripping time is controlled to be no more than 70 ℃, the azobisisobutyronitrile can be added in batches in 3-4 batches in the process of dripping oxalyl chloride and the reaction, 0.15g of azobisisobutyronitrile is added altogether, the reaction is stopped after the dripping is completed and the reaction is monitored to be completed for 5 hours, and the chlorobenzene is removed by reduced pressure distillation, so as to obtain the 2, 4-dimethoxy benzoyl chloride. The obtained 2, 4-dimethoxy benzoyl chloride is added into enough water for hydrolysis (the water is calculated according to the molar quantity and is more than the molar quantity of the 2, 4-dimethoxy benzoyl chloride), and the mixture is filtered, washed, recrystallized by water and dried to obtain 17.2g of 2, 4-dimethoxy benzoic acid. Yield 95.2% and purity 99.5%
Example 2, 13.8g of m-xylylene ether is put into a three-neck flask, 0.05g of azodiisobutyronitrile is added, the magnetic stirrer is put into the flask and is started to stir, when the temperature is raised to 50 ℃ as indicated by heating, a solution consisting of 12.8g of oxalyl chloride and 15ml of toluene is started to be added dropwise for 15 minutes, the temperature is controlled to be not more than 70 ℃, and 3-4 batches of azodiisobutyronitrile are added in the process of dropwise oxalyl chloride and the reaction, 0.15g of azodiisobutyronitrile is added altogether, the reaction is stopped for 5 hours at 70 ℃ after the dropwise addition, and toluene is removed by reduced pressure distillation, so that 2, 4-dimethoxy benzoyl chloride is obtained. The obtained 2, 4-dimethoxy benzoyl chloride is added into enough water for hydrolysis, filtered, washed with water, recrystallized with water and dried to obtain 17.1g of 2, 4-dimethoxy benzoic acid with the yield of 95 percent and the purity of 99.5 percent.
Example 3, 13.8g of m-xylylene ether is put into a three-neck flask, 0.05g of azodiisobutyronitrile is added, the stirring is started, after the stirring is started, when the temperature is raised to 50 ℃ as indicated, the solution consisting of 12.8g of oxalyl chloride and 15ml of 1, 2-dichloroethane is started to be dripped for 15 minutes, the temperature is controlled to be not more than 70 ℃, the azodiisobutyronitrile is added in batches in the dripping process, 3-4 batches can be added, 0.15g of azodiisobutyronitrile is added altogether, the reaction is stopped after the dripping is finished, the reaction is stopped at 70 ℃, and the 1, 2-dichloroethane is removed by reduced pressure distillation, so as to obtain the 2, 4-dimethoxy benzoyl chloride. And adding the obtained 2, 4-dimethoxy benzoyl chloride into enough water for hydrolysis, filtering to obtain a 2, 4-dimethoxy benzoic acid crude product, and adding water for recrystallization to obtain the 2, 4-dimethoxy benzoic acid, wherein the yield is 96 percent and the purity is 99.5 percent.
Example 4, 13.8g of m-xylylene ether is put into a three-neck flask, 0.05g of azodiisobutyronitrile is added, the magnetic stirrer is put into the flask, stirring is started, when the temperature is raised to 50 ℃ as indicated by heating, the solution consisting of 12.8g of oxalyl chloride and 15ml of dimethylbenzene is started to be dripped for 15 minutes, the temperature is controlled to be not more than 70 ℃ for reaction, 3-4 batches of azodiisobutyronitrile are added in batches in the process of dripping oxalyl chloride and the reaction, 0.15g of azodiisobutyronitrile is added altogether, the temperature is controlled to be 70 ℃ for reaction for 5 hours after the dripping is finished, the reaction is stopped, and the dimethylbenzene is removed by reduced pressure distillation, so that 2, 4-dimethoxy benzoyl chloride is obtained. And adding the obtained 2, 4-dimethoxy benzoyl chloride into enough water for hydrolysis, filtering to obtain a 2, 4-dimethoxy benzoic acid crude product, and adding water for recrystallization to obtain the 2, 4-dimethoxy benzoic acid, wherein the yield is 95.7%, and the purity is 99.5%.
Example 5, 13.8g of m-xylylene ether is put into a three-neck flask, 0.05g of azodiisobutyronitrile is added, after a magnetic stirrer is put and stirring is started, when the temperature is raised to 50 ℃ as indicated by heating, a solution consisting of 12.8g of oxalyl chloride and 15ml of carbon tetrachloride is started to be added dropwise for 15 minutes, the temperature is controlled to be not more than 70 ℃, azodiisobutyronitrile is added in batches in the processes of dropwise oxalyl chloride and reaction, 3-4 batches of azodiisobutyronitrile can be added, 0.15g of azodiisobutyronitrile is added altogether, the reaction is stopped for 5 hours at 70 ℃ after the dropwise addition, and the carbon tetrachloride is removed by reduced pressure distillation, so that 2, 4-dimethoxy benzoyl chloride is obtained. And adding the obtained 2, 4-dimethoxy benzoyl chloride into enough water for hydrolysis, filtering to obtain a 2, 4-dimethoxy benzoic acid crude product, and adding water for recrystallization to obtain the 2, 4-dimethoxy benzoic acid, wherein the yield is 96.1 percent and the purity is 99.5 percent.
Example 6, 13.8g of m-xylylene ether is put into a three-neck flask, 0.05g of azobisisobutyronitrile is added, the magnetic stirrer is started to stir, when the temperature is raised to 50 ℃ as indicated by heating, a solution consisting of 12.8g of oxalyl chloride and 15ml of chloroform is started to be added dropwise for 15 minutes, the temperature is controlled to be not more than 70 ℃, 3-4 batches of azobisisobutyronitrile can be added in a batch-wise manner during the processes of dropwise adding oxalyl chloride and reacting, 0.15g of azobisisobutyronitrile is added altogether, the reaction is stopped for 5 hours at 70 ℃ after the dropwise adding, and the chloroform is removed by reduced pressure distillation to obtain 2, 4-dimethoxy benzoyl chloride. And adding the obtained 2, 4-dimethoxy benzoyl chloride into enough water for hydrolysis, filtering to obtain a 2, 4-dimethoxy benzoic acid crude product, and adding water for recrystallization to obtain the 2, 4-dimethoxy benzoic acid, wherein the yield is 95.8%, and the purity is 99.5%.
Example 7, 13.8g of m-xylylene ether is put into a three-neck flask, 0.05g of azodiisobutyronitrile is added, the magnetic stirrer is put into the flask and is started to stir, when the temperature is raised to the indicated temperature of 60 ℃, the solution consisting of 12.8g of oxalyl chloride and 15ml of dichlorobenzene is started to be dripped for 15 minutes, the temperature is controlled to be not higher than 90 ℃, the azodiisobutyronitrile is added in batches in the dripping process of oxalyl chloride and the reaction process, 3-4 batches of azodiisobutyronitrile can be added, 0.15g of azodiisobutyronitrile is added altogether, the reaction is stopped for 5 hours at the temperature of 90 ℃ after the dripping process, and the dichlorobenzene is removed by reduced pressure distillation, so that 2, 4-dimethoxy benzoyl chloride is obtained. And adding the obtained 2, 4-dimethoxy benzoyl chloride into enough water for hydrolysis, filtering to obtain a 2, 4-dimethoxy benzoic acid crude product, and adding water for recrystallization to obtain the 2, 4-dimethoxy benzoic acid, wherein the yield is 95 percent and the purity is 99.5 percent.
Example 8, 13.8g of m-xylylene ether is put into a three-neck flask, 0.05g of azodiisobutyronitrile is added, the magnetic stirrer is put into the flask and is started to stir, when the temperature is raised to the indicated temperature of 60 ℃, the solution consisting of 12.8g of oxalyl chloride and 15ml of petroleum ether is started to be dripped for 15 minutes, the temperature is controlled to be not higher than 90 ℃, the azodiisobutyronitrile is added in batches in the dripping process of oxalyl chloride and the reaction process, 3-4 batches of azodiisobutyronitrile can be added, 0.15g of azodiisobutyronitrile is added altogether, the reaction is stopped for 5 hours at the temperature of 90 ℃ after the dripping process is finished, and the petroleum ether is removed by reduced pressure distillation, so that 2, 4-dimethoxy benzoyl chloride is obtained. And adding the obtained 2, 4-dimethoxy benzoyl chloride into enough water for hydrolysis, filtering to obtain a 2, 4-dimethoxy benzoic acid crude product, and adding water for recrystallization to obtain the 2, 4-dimethoxy benzoic acid, wherein the yield is 95.1 percent and the purity is 99.5 percent.
Example 9
13.8g of m-xylylene ether is put into a three-neck flask, 0.05g of benzoyl peroxide is added, the magnetic stirrer is put into the flask, stirring is started, when the temperature is raised to 60 ℃ as indicated by heating, the solution consisting of 12.8g of oxalyl chloride and 15ml of petroleum ether is started to be dripped for 15 minutes, the temperature is controlled to be not higher than 90 ℃, benzoyl peroxide is added in batches in the dripping process of oxalyl chloride and the reaction process, 0.276g of benzoyl peroxide can be added in batches of 3-4, the reaction is stopped after the dripping is finished at 90 ℃ for 5 hours, and the petroleum ether is removed by reduced pressure distillation, so that 2, 4-dimethoxy benzoyl chloride is obtained. And adding the obtained 2, 4-dimethoxy benzoyl chloride into enough water for hydrolysis, filtering to obtain a 2, 4-dimethoxy benzoic acid crude product, and adding water for recrystallization to obtain the 2, 4-dimethoxy benzoic acid, wherein the yield is 94.8%, and the purity is 99.5%.
Example 10
13.8g of m-xylylene ether is put into a three-neck flask, 0.05g of azodiisobutyronitrile is added, the magnetic stirrer is started to stir, when the temperature is raised to 50 ℃ as indicated by heating, 12.8g of oxalyl chloride and 15ml of toluene are added dropwise for 15 minutes, the temperature is controlled to be not more than 70 ℃, 3-4 batches of azodiisobutyronitrile can be added in a batch mode in the processes of dropwise adding oxalyl chloride and reacting, 0.138g of azodiisobutyronitrile is added, the temperature is controlled to be 70 ℃ after the dropwise adding is finished, the reaction is stopped, and toluene is removed by reduced pressure distillation, so that 2, 4-dimethoxy benzoyl chloride is obtained. The obtained 2, 4-dimethoxy benzoyl chloride is added into enough water for hydrolysis, filtered, washed with water, recrystallized with water and dried to obtain 17.1g of 2, 4-dimethoxy benzoic acid, the yield is 95.1%, and the purity is 99.5%.
Example 11
13.8g of m-xylylene ether is put into a three-neck flask, 0.05g of azodiisobutyronitrile is added, the magnetic stirrer is started to stir, when the temperature is raised to 50 ℃ as indicated by heating, 12.69g of oxalyl chloride and 15ml of toluene are added dropwise for 15 minutes, the temperature is controlled to be not more than 70 ℃, 3-4 batches of azodiisobutyronitrile can be added in a batch mode in the processes of dropwise adding oxalyl chloride and reacting, 0.15g of azodiisobutyronitrile is added, the reaction is stopped after the dropwise adding is finished, the temperature is controlled to be 70 ℃ for reacting for 5 hours, and the toluene is removed by reduced pressure distillation, so that 2, 4-dimethoxy benzoyl chloride is obtained. The obtained 2, 4-dimethoxy benzoyl chloride was added to a sufficient amount of water for hydrolysis, filtered, washed with water, recrystallized with water and dried to obtain 17.1g of 2, 4-dimethoxy benzoic acid, with a yield of 94.8% and a purity of 99.5%.
Example 12
13.8g of m-xylylene ether is put into a three-neck flask, 0.05g of azodiisobutyronitrile is added, the magnetic stirrer is started to stir, when the temperature is raised to 50 ℃ as indicated by heating, a solution consisting of 15.2g of oxalyl chloride and 15ml of toluene is started to be added dropwise for 15 minutes, the temperature is controlled to be not more than 70 ℃, the azodiisobutyronitrile can be added in 3-4 batches in a batch-by-batch mode in the process of dropwise adding oxalyl chloride and the reaction, 0.15g of azodiisobutyronitrile is added altogether, the reaction is stopped after the dropwise adding is finished, the reaction is stopped at 70 ℃ and the toluene is removed by reduced pressure distillation, so that 2, 4-dimethoxy benzoyl chloride is obtained. The obtained 2, 4-dimethoxy benzoyl chloride is added into enough water for hydrolysis, filtered, washed with water, recrystallized with water and dried to obtain 17.1g of 2, 4-dimethoxy benzoic acid, the yield is 95.3%, and the purity is 99.5%.
Example 13
13.8g of m-xylylene ether is put into a three-neck flask, 0.05g of benzoyl peroxide is added, the magnetic stirrer is put into the flask, stirring is started, when the temperature is raised to 60 ℃ as indicated by heating, the solution consisting of 12.8g of oxalyl chloride and 15ml of petroleum ether is started to be dropwise added for 15 minutes, the temperature is controlled to be not higher than 90 ℃, benzoyl peroxide is added in batches in the process of dropwise adding oxalyl chloride and reacting, 0.15g of benzoyl peroxide can be added in batches of 3-4, the reaction is stopped after the dropwise adding, the reaction is stopped at 90 ℃ for 5 hours, and the petroleum ether is removed by reduced pressure distillation, so that 2, 4-dimethoxy benzoyl chloride is obtained. And adding the obtained 2, 4-dimethoxy benzoyl chloride into enough water for hydrolysis, filtering to obtain a 2, 4-dimethoxy benzoic acid crude product, and adding water for recrystallization to obtain the 2, 4-dimethoxy benzoic acid, wherein the yield is 94.9% and the purity is 99.5%.
The present invention is not limited to the above-described embodiments, and those skilled in the art will appreciate that: many changes, modifications, substitutions and variations may be made to the embodiments without departing from the spirit and principles of the invention, the scope of which is defined by the claims and their equivalents.

Claims (8)

1. A method for synthesizing 2, 4-dimethoxy benzoyl chloride, which is characterized by comprising the following steps: the method comprises the steps of taking m-xylylene ether and oxalyl chloride as raw materials, reacting in the presence of an organic solvent and a catalyst until the reaction is complete, and then removing the organic solvent by reduced pressure distillation to obtain 2, 4-dimethoxy benzoyl chloride, wherein the catalyst is azodiisobutyronitrile or benzoyl peroxide.
2. The method for synthesizing 2, 4-dimethoxy benzoyl chloride according to claim 1, wherein: the dosage of the catalyst is 1% -2% of the mass of the m-xylylene glycol methyl ether.
3. The method for synthesizing 2, 4-dimethoxy benzoyl chloride according to claim 2, wherein: the catalyst is added in portions.
4. A method for synthesizing 2, 4-dimethoxybenzoyl chloride according to claim 3, characterized in that: the organic solvent is one of toluene, xylene, 1, 2-dichloroethane, carbon tetrachloride, chloroform, dichlorobenzene and petroleum ether.
5. The method for synthesizing 2, 4-dimethoxy benzoyl chloride according to claim 4, wherein: the molar ratio of the m-xylylene ether to the oxalyl chloride is 1:1-1:1.2.
6. The method for synthesizing 2, 4-dimethoxy benzoyl chloride according to any one of claims 1 to 5, wherein the operation steps are: adding m-xylylene ether into a reaction vessel, stirring, adding part of catalyst, heating to 50-60 ℃, dropwise adding a mixed solution of oxalyl chloride and an organic solvent, controlling the temperature to react at 70-90 ℃ after the dropwise adding, adding the rest catalyst in batches in the process of dropwise adding oxalyl chloride and the reaction, and removing the organic solvent by reduced pressure distillation after the reaction is completed to obtain the 2, 4-dimethoxy benzoyl chloride.
7. A method for synthesizing 2, 4-dimethoxy benzoic acid is characterized in that: the process according to any one of claims 1 to 6, wherein 2, 4-dimethoxybenzoyl chloride is prepared first, hydrolyzed with water, and then recrystallized to give 2, 4-dimethoxybenzoic acid.
8. The method for synthesizing 2, 4-dimethoxybenzoic acid according to claim 7, wherein: the solvent used for recrystallization is water.
CN202310081137.3A 2023-02-08 2023-02-08 Method for synthesizing 2, 4-dimethoxy benzoyl chloride and 2, 4-dimethoxy benzoic acid Pending CN116253638A (en)

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