CN111574368A - Synthesis method of methyl 5-tert-butyl-2-hydroxybenzoate - Google Patents
Synthesis method of methyl 5-tert-butyl-2-hydroxybenzoate Download PDFInfo
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- C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
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- C07C67/52—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
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Abstract
The invention discloses a synthesis method of 5-tert-butyl-2-hydroxybenzoic acid methyl ester, belonging to the technical field of organic synthesis, comprising the following steps: s1, preparing a mixture of a compound of formula (I), a compound of formula (II) and a compound of formula (III) by taking methyl salicylate and tert-butyl alcohol as raw materials under the catalysis of concentrated sulfuric acid; s2, carrying out rearrangement reaction on the mixture prepared in the S1 under the catalysis of Lewis acid, and carrying out post-treatment to prepare a pure product of the compound shown in the formula (I), namely 5-tert-butyl-2-hydroxybenzoic acid methyl ester; the synthesis method of the 5-tert-butyl-2-hydroxybenzoic acid methyl ester has the advantages of low production cost, novel preparation line, simple equipment and easy industrial production, and can be widely applied to the field of fine chemical production.
Description
Technical Field
The invention belongs to the technical field of organic synthesis, and particularly relates to a synthesis method of 5-tert-butyl-2-hydroxybenzoic acid methyl ester.
Background
Methyl 5-tert-butyl-2-hydroxybenzoate is an important organic chemical product, can be used as a stabilizer for food, fat and the like, and is also an important raw material for organic synthesis. Similar compounds are produced, and the mainstream literature reports that Friedel-crafts alkylation reaction is carried out by using bromo-tert-butane or chloro-tert-butane and methyl salicylate, and catalytic reaction is also carried out by using novel solid acid or inorganic polymer acid. The method of using halogenated tert-butane is active in property and releases toxic phosgene when heated, so that the requirement on equipment is high, and equipment investment is stumbling stone which hinders industrialization. The novel solid acid and inorganic polymer acid belong to two-phase reaction, the market supply of the solid acid is limited at present, and the large-scale industrial production is limited. The related documents are: 【1】 A method for catalytically synthesizing a tert-butylphenol compound, which comprises the steps of neying, periflying and tension wave, and CN 200610124663.【2】 Nakamura, h.; hase gawa.H.; satoe.; sato k. jp Pat.62081338, 1987. 【3】 Curt B.Campbell, Antali Onopchenko, and Donald C.Young, Ind.Eng.chem.Res.1990,29,642 Across 647. The literature [ 1 ] reports that the synthesis of tert-butylphenol compounds by using high molecular weight polymer catalysts has the obvious disadvantage of high catalyst cost, no large supply is available in the market at present, and large-scale industrialization is difficult to realize.
The document [ 2 ] is phosphoric acid catalysis, the consumption of phosphoric acid is large, the conversion speed is slow through verification, and the raw material residue is more than 50% after 10 hours of reaction. The selectivity is poor, and the purification yield is less than 40 percent.
The document [ 3 ] is catalyzed by polystyrene sulfonic acid resin (Amberlyst-15), the reaction is poorly selective, the monoalkylated product is predominant, and the yield is only 49%.
On the basis of the existing industrialization, how to improve the process and reduce the cost is a main problem.
Disclosure of Invention
In order to solve the problems, the invention provides a synthesis method of 5-tert-butyl-2-hydroxybenzoic acid methyl ester, which comprises the steps of preparing a crude product by using a common acid catalyst through process improvement, and then carrying out catalytic rearrangement by using Lewis acid to obtain the 5-tert-butyl-2-hydroxybenzoic acid methyl ester with higher yield and purity; the whole process has controllable acid consumption, high reaction speed, simple whole process flow, easy realization of industrialization and very obvious cost advantage.
A synthetic method of methyl 5-tert-butyl-2-hydroxybenzoate comprises the following steps:
s1, preparing a mixture of a compound of formula (I), a compound of formula (II) and a compound of formula (III) by taking methyl salicylate and tert-butyl alcohol as raw materials under the catalysis of concentrated sulfuric acid;
s2, carrying out rearrangement reaction on the mixture prepared in the S1 under the catalysis of Lewis acid, and carrying out post-treatment to prepare a pure product of the compound shown in the formula (I), namely 5-tert-butyl-2-hydroxybenzoic acid methyl ester;
the synthetic route is as follows:
preferably, S1 specifically includes the following steps:
after mixing methyl salicylate and tert-butyl alcohol, controlling the temperature to be 0-30 ℃, adding concentrated sulfuric acid, continuing to react, and after the reaction is finished, carrying out post-treatment on reaction liquid to obtain a mixture of a compound of formula (I), a compound of formula (II) and a compound of formula (III).
Preferably, the molar ratio of the methyl salicylate to the concentrated sulfuric acid is 1: 1-5; the mass ratio of the methyl salicylate to the tert-butyl alcohol is 1: 1.46.
Preferably, in S1, the post-treatment of the reaction solution includes cooling, extraction, washing the organic phase with water to pH 5 to 6, drying, filtering, and concentrating the filtrate.
Preferably, the reagent used for extraction is n-hexane.
Preferably, S2 specifically includes the following steps:
and dissolving Lewis acid in dichloromethane, adding the mixture prepared by S1, controlling the temperature to be 35-40 ℃ for reaction, and after the reaction is finished, carrying out post-treatment on the reaction liquid to prepare the pure 5-tert-butyl-2-hydroxybenzoic acid methyl ester product.
Preferably, in the mixture prepared in S1, the mass fraction of methyl 3, 5-di-tert-butyl-2-hydroxybenzoate is 31.1205%, and the molar ratio of methyl 3, 5-di-tert-butyl-2-hydroxybenzoate to Lewis acid is 1: 0.5 to 2.
Preferably, in S2, after the reaction is completed, the reaction solution is quenched with an acid, left to stand, extracted with an organic phase, washed with an acid, washed with water to a pH of 5 to 6, separated, dried with an organic phase, filtered, concentrated in the filtrate, and distilled.
Preferably, the lewis acid is anhydrous zinc chloride, anhydrous ferric chloride, boron trifluoride or anhydrous aluminum trichloride.
Compared with the prior art, the invention has the beneficial effects that:
the invention uses common acid to catalyze, prepares a crude product, and then uses Lewis acid to catalyze and rearrange to obtain the 5-tert-butyl-2-hydroxybenzoic acid methyl ester with higher yield and purity. The confirmation proves that the using amount of the acid in the whole process is controllable, the reaction speed is high, the whole process flow is simple, the industrialization is easy to realize, and the cost has very remarkable advantages. The synthesis method of the 5-tert-butyl-2-hydroxybenzoic acid methyl ester has the advantages of low production cost, novel preparation line, simple equipment and easy industrial production, and can be widely applied to the field of fine chemical production.
Drawings
FIG. 1 is a LC spectrum of a mixture of methyl 5-tert-butyl-2-hydroxybenzoate, methyl 3-tert-butyl-2-hydroxybenzoate and methyl 3, 5-di-tert-butyl-2-hydroxybenzoate in example 1 of the present invention;
FIG. 2 is a LC spectrum of the purification of methyl 5-tert-butyl-2-hydroxybenzoate in example 1 of the present invention;
FIG. 3 is a HNMR spectrum of methyl 5-tert-butyl-2-hydroxybenzoate in example 1 of the present invention.
Detailed Description
In order to make the technical solutions of the present invention better understood and implemented by those skilled in the art, the present invention is further described below with reference to the following specific embodiments and the accompanying drawings, but the embodiments are not meant to limit the present invention.
Example 1
The specific synthetic process of the synthetic method of 5-tert-butyl-2-hydroxybenzoic acid methyl ester is as follows:
1) preparation of a mixture of methyl 5-tert-butyl-2-hydroxybenzoate, methyl 3, 5-di-tert-butyl-2-hydroxybenzoate:
200g of methyl o-hydroxybenzoate and 292.3g of tert-butyl alcohol are added into a 1L three-necked bottle with a stirrer and a thermometer under stirring, the system is cooled to 5-15 ℃ by an ice bath after the addition is finished, 386.3g of concentrated sulfuric acid is added dropwise, the temperature is controlled to 5-15 ℃ during the process, the reaction is stirred after the addition is finished, and the reaction is stopped until the content of the raw material methyl o-hydroxybenzoate LC is less than 5.0%.
2) Work-up of a mixture of methyl 5-tert-butyl-2-hydroxybenzoate, methyl 3, 5-di-tert-butyl-2-hydroxybenzoate: pouring the reaction liquid into 2L of ice water, controlling the temperature to be 10-20 ℃, adding 1L of n-hexane for extraction, separating liquid, temporarily placing an organic phase, adding 500ml of n-hexane into a water phase for extraction once, separating liquid, combining organic phases, washing the organic phases for 500ml 2 times until the pH value is 5-6, adding anhydrous magnesium sulfate into the organic phases, stirring and drying for 4h, filtering, leaching a filter cake once with 100ml of n-hexane, combining the organic phases, concentrating at 40-45 ℃ under reduced pressure (-0.09MPa to-0.08 MPa) until the organic phases are not discharged to obtain 474g of colorless liquid, obtaining 474g of 5-tert-butyl-2-hydroxybenzoic acid methyl ester LC (being 49.2995%), 3-tert-butyl-2-hydroxybenzoic acid methyl ester LC (being 16.8214%), and 3, 5-di-tert-butyl-2-hydroxybenzoic acid methyl ester LC (being 31.1205%), and carrying out impurity conversion directly on the next step; the reaction equation is as follows:
3) preparation of methyl 5-tert-butyl-2-hydroxybenzoate: adding 2100ml of dichloromethane into a 5L three-necked bottle with a stirring thermometer while stirring, adding 257.6g of aluminum trichloride, stirring for 30min, dropwise adding 474g of a mixture of methyl 5-tert-butyl-2-hydroxybenzoate, methyl 3-tert-butyl-2-hydroxybenzoate and methyl 3, 5-di-tert-butyl-2-hydroxybenzoate, controlling the temperature of 15-25 ℃ in the process, after the feeding is finished, starting heating to reflux for 35-40 ℃, stirring for reacting for 2h, and stopping the reaction.
4) Aftertreatment of methyl 5-tert-butyl-2-hydroxybenzoate:
and pouring the reaction solution into prepared 2.5L of diluted hydrochloric acid for quenching, stirring for 10min, separating, temporarily placing an organic phase, adding 750ml of dichloromethane into a water phase for 2 times of extraction, combining the organic phases, washing once with 1L of diluted hydrochloric acid, separating, washing the organic phase with 1L of water for 2 times until the pH value is 5-6, separating, stirring and drying the organic phase with 30g of anhydrous magnesium sulfate for 2h, filtering, leaching a filter cake once with 100ml of dichloromethane, concentrating the organic phase under reduced pressure (35-45 ℃, minus 0.08-minus 0.07MPa) until the organic phase cannot be separated (about 2h), and obtaining 382g of crude product.
5) Purification of methyl 5-tert-butyl-2-hydroxybenzoate: and (3) distilling 382g of the crude product obtained by the previous step in high vacuum, wherein the column height is 15cm, the external temperature is 110-130 ℃, the outlet temperature is 90-100 ℃, the vacuum degree is 30-50 Pa, and 256g of main fraction is distilled.
256g of distilled main fraction obtained by distillation is added with 256ml of normal hexane, the mixture is stirred evenly, the mixture is placed in a refrigerator for freezing (-15 to-10 ℃) for about 10 hours, a large amount of solid is separated out, the filtration is carried out, mother liquor is concentrated and dried temporarily, 156g of filtration solid is obtained, the drying material is baked for 8 hours at the temperature of 40 to 45 ℃, 138.1g of off-white solid is obtained, and LC (liquid chromatography) is 98.6395%.
6) Mother liquor recovery: and (3) concentrating the mother liquor obtained by recrystallization under negative pressure (35-45 ℃ and-0.08-0.07 MPa) until the mother liquor is not discharged, adding 100ml of n-hexane, uniformly stirring, placing in a refrigerator for freezing (15 ℃ to-10 ℃) for about 10 hours, separating out solids, filtering, and drying the obtained solids for 8 hours at 40-45 ℃ to obtain 15g of off-white solids, wherein LC (liquid chromatography) is 99.22%.
HNMR:10.596ppm is phenolic hydroxyl-H; 7.819 ppm-6.914 ppm is-H on benzene ring; 3.952ppm is-H on the methyl group of the carboxylic acid methyl ester; 1.303ppm of 9-H's which are tert-butyl groups.
The reaction equation is as follows:
example 2
The specific synthetic process of the synthetic method of 5-tert-butyl-2-hydroxybenzoic acid methyl ester is as follows:
1) preparation of a mixture of methyl 5-tert-butyl-2-hydroxybenzoate, methyl 3, 5-di-tert-butyl-2-hydroxybenzoate:
200g of methyl o-hydroxybenzoate and 292.3g of tert-butyl alcohol are added into a 1L three-necked bottle with a stirrer and a thermometer under stirring, the system is cooled to 5-15 ℃ by an ice bath after the addition is finished, 128.8g of concentrated sulfuric acid is added dropwise, the temperature is controlled to 5-15 ℃ during the process, the reaction is stirred after the addition is finished, and the reaction is stopped until the content of the raw material methyl o-hydroxybenzoate LC is less than 5.0%.
2) Work-up of a mixture of methyl 5-tert-butyl-2-hydroxybenzoate, methyl 3, 5-di-tert-butyl-2-hydroxybenzoate: pouring the reaction liquid into 2L of ice water, controlling the temperature to be 10-20 ℃, adding 1L of n-hexane for extraction, separating liquid, temporarily placing an organic phase, adding 500ml of n-hexane into a water phase for extraction once, separating liquid, combining organic phases, washing the organic phases for 500ml 2 times until the pH value is 5-6, adding anhydrous magnesium sulfate into the organic phases, stirring and drying for 4h, filtering, leaching a filter cake once with 100ml of n-hexane, combining the organic phases, concentrating at 40-45 ℃ under reduced pressure (-0.09MPa to-0.08 MPa) until no colorless liquid is obtained, obtaining 465g of colorless liquid, obtaining 5-tert-butyl-2-hydroxybenzoic acid methyl ester LC (being 37.9825%), 3-tert-butyl-2-hydroxybenzoic acid methyl ester LC (being 19.9361%), and 3, 5-di-tert-butyl-2-hydroxybenzoic acid methyl ester LC (being 32.2665%), and carrying out the next step of purification directly; the reaction equation is as follows:
3) preparation of methyl 5-tert-butyl-2-hydroxybenzoate: adding 2100ml of dichloromethane into a 5L three-necked bottle with a stirring thermometer while stirring, adding 85.87g of aluminum trichloride, stirring for 30min, dropwise adding 465g of a mixture of 5-tert-butyl-2-hydroxybenzoic acid methyl ester, 3-tert-butyl-2-hydroxybenzoic acid methyl ester and 3, 5-di-tert-butyl-2-hydroxybenzoic acid methyl ester, controlling the temperature to be 15-25 ℃, after the feeding is finished, starting heating to reflux for 35-40 ℃, stirring for reacting for 2h, and stopping the reaction.
4) Aftertreatment of methyl 5-tert-butyl-2-hydroxybenzoate:
and pouring the reaction solution into prepared 2.5L of diluted hydrochloric acid for quenching, stirring for 10min, separating, temporarily placing an organic phase, adding 750ml of dichloromethane into a water phase for 2 times of extraction, combining the organic phases, washing once with 1L of diluted hydrochloric acid, separating, washing the organic phase with 1L of water for 2 times until the pH value is 5-6, separating, stirring and drying the organic phase with 30g of anhydrous magnesium sulfate for 2h, filtering, leaching a filter cake once with 100ml of dichloromethane, concentrating the organic phase under reduced pressure (35-45 ℃, minus 0.08-minus 0.07MPa) until the organic phase cannot be separated (about 2h), and obtaining 342g of crude product.
5) Purification of methyl 5-tert-butyl-2-hydroxybenzoate: carrying out high vacuum distillation on 342g of the obtained crude product, wherein the column height is 15cm, the external temperature is 110-130 ℃, the outlet temperature is 90-100 ℃, the vacuum degree is 30-50 Pa, and distilling out 211g of main fraction.
211g of distilled main fraction 211g is added with 211ml of normal hexane, the mixture is stirred evenly, the mixture is placed in a refrigerator for freezing for about 10 hours at the temperature of minus 15 to minus 10 ℃, a large amount of solid is separated out, the filtration is carried out, the mother liquor is concentrated and dried for temporary placement, 126g of filtration solid is obtained, the material is dried for 8 hours at the temperature of 40 to 45 ℃, 109.4g of off-white solid is obtained, and the content is qualified.
6) Mother liquor recovery: and (3) concentrating the mother liquor obtained by recrystallization under negative pressure (35-45 ℃ and-0.08-0.07 MPa) until no more than 100ml of n-hexane is obtained, uniformly stirring, placing in a refrigerator for freezing for about 10 hours at (-15 ℃ to-10 ℃), separating out solids, filtering, and drying the obtained solids for 8 hours at 40-45 ℃ to obtain 11g of off-white solids with qualified content.
The reaction equation is as follows:
it will be apparent to those skilled in the art that various changes and modifications may be made in the present invention without departing from the spirit and scope of the invention. Thus, it is intended that such changes and modifications be included within the scope of the appended claims and their equivalents.
Claims (9)
1. A synthesis method of methyl 5-tert-butyl-2-hydroxybenzoate is characterized by comprising the following steps:
s1, preparing a mixture of a compound of formula (I), a compound of formula (II) and a compound of formula (III) by taking methyl salicylate and tert-butyl alcohol as raw materials under the catalysis of concentrated sulfuric acid;
s2, carrying out rearrangement reaction on the mixture prepared in the S1 under the catalysis of Lewis acid, and carrying out post-treatment to prepare a pure product of the compound shown in the formula (I), namely 5-tert-butyl-2-hydroxybenzoic acid methyl ester;
the synthetic route is as follows:
2. the method for synthesizing methyl 5-tert-butyl-2-hydroxybenzoate according to claim 1, wherein the S1 specifically comprises the following steps:
after mixing methyl salicylate and tert-butyl alcohol, controlling the temperature to be 0-30 ℃, adding concentrated sulfuric acid, controlling the temperature to be 10 +/-5 ℃ in the process, continuing to react in the temperature range, and after the reaction is finished, carrying out post-treatment on reaction liquid to obtain a mixture of a compound of formula (I), a compound of formula (II) and a compound of formula (III).
3. The synthesis method of methyl 5-tert-butyl-2-hydroxybenzoate according to claim 2, wherein the molar ratio of methyl salicylate to concentrated sulfuric acid is 1: 1-5; the mass ratio of the methyl salicylate to the tert-butyl alcohol is 1: 1.46.
4. The method for synthesizing methyl 5-tert-butyl-2-hydroxybenzoate according to claim 2, wherein in S1, the post-treatment of the reaction solution comprises cooling, extraction, washing the organic phase with water to pH 5-6, drying, filtering and concentrating the filtrate.
5. The method for synthesizing methyl 5-tert-butyl-2-hydroxybenzoate according to claim 4, wherein the reagent used for extraction is n-hexane.
6. The method for synthesizing methyl 5-tert-butyl-2-hydroxybenzoate according to claim 1, wherein the S2 specifically comprises the following steps:
dissolving Lewis acid in dichloromethane, adding the mixture prepared by S1, controlling the temperature to be 38 +/-2 ℃ for reaction, and after the reaction is finished, carrying out post-treatment on the reaction liquid to prepare the pure 5-tert-butyl-2-hydroxybenzoic acid methyl ester.
7. The method of synthesizing methyl 5-tert-butyl-2-hydroxybenzoate according to claim 6, wherein the mass fraction of methyl 3, 5-di-tert-butyl-2-hydroxybenzoate in the mixture prepared by S1 is 31.1205%, and the molar ratio of methyl 3, 5-di-tert-butyl-2-hydroxybenzoate to Lewis acid is 1: 0.5 to 2.
8. The method of synthesizing methyl 5-tert-butyl-2-hydroxybenzoate according to claim 6, wherein in S2, after the reaction is completed, the reaction solution is quenched with an acid, allowed to stand, extracted with an organic phase, washed with an acid, washed with water to a pH of 5 to 6, separated, dried with an organic phase, filtered, concentrated in filtrate, and distilled.
9. The method of synthesizing methyl 5-tert-butyl-2-hydroxybenzoate according to claim 6, wherein the Lewis acid is anhydrous zinc chloride, anhydrous ferric chloride, boron trifluoride or anhydrous aluminum trichloride.
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| CN112479877A (en) * | 2020-12-21 | 2021-03-12 | 江苏极易新材料有限公司 | Synthesis process of 3- (3-tert-butyl-4-hydroxy) methyl phenylpropionate |
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