CN105732394A - 3-methoxy-4-nitrobenzoic acid and preparation method thereof - Google Patents
3-methoxy-4-nitrobenzoic acid and preparation method thereof Download PDFInfo
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- CN105732394A CN105732394A CN201610171900.1A CN201610171900A CN105732394A CN 105732394 A CN105732394 A CN 105732394A CN 201610171900 A CN201610171900 A CN 201610171900A CN 105732394 A CN105732394 A CN 105732394A
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- methoxyl group
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
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Abstract
The invention aims at providing 3-methoxy-4-nitrobenzoic acid and a preparation method thereof. The preparation method comprises the steps of firstly carrying out bromination reaction on p-nitrobenzoic acid to substitute the ortho-position of nitro with bromine, and reacting by virtue of products and sodium methoxide to substitute bromine with methoxy, so as to obtain the target product 3-methoxy-4-nitrobenzoic acid. The preparation method is simple, required reaction conditions are mild, the raw materials and catalysts utilized in the reaction process are cheap and easily available, and the production cost is relatively low; and the preparation method is very applicable to large-scale industrial production.
Description
Technical field:
The present invention relates to biomedicine technical field, particularly relate to a kind of 3-methoxyl group-4-nitre
Yl benzoic acid and preparation method thereof.
Background technology:
Nitrodracylic acid is in the middle of a kind of important fine organic product industry and medical industry
Body, can further prepare the most important medicine or fine organic product with it for raw material.It
Can be used for producing procaine class medicine, folic acid, benzocaine and some treatment hypertension
Medicine, simultaneously it or the required raw material of the 'Inshuzhi ' of scalable plant growing.Wherein 3 take
The derivant of the Nitrodracylic acid in generation is also a kind of important medicine intermediate, industrial water requirement
The most greatly, the concern widely research of its preparation method being also subject to.
The wherein preparation method of 3-methoxyl group-4-nitrobenzoic acid, the at home introduction in patent
Less.Chinese patent 201310235618.1 describes a kind of nitric acid oxidation method and prepares 3-methyl
The method of-4-nitrobenzoic acid, with dust technology as oxidant, 2,4-dimethyl nitrobenzenes are base
This raw material, feeds intake through peroxidization, the acid out that neutralizes, extract, decolour, and conservative control
Ratio, reaction temperature, reaction pressure and response time.Improve the conversion ratio of reaction, decrease
The yield of by-product.But it is specific to the Nitrodracylic acid derivant of 3 methoxy substitutions,
Due to the particularity of methoxyl group, the productivity in its preparation process still has much room for improvement.
Summary of the invention:
It is an object of the invention to provide a kind of 3-methoxyl group-4-nitrobenzoic acid and preparation side thereof
Method, the operational approach of the method is simple, required reflection mild condition, raw material and course of reaction
The catalyst of middle use is cheap and easy to get, and production cost is relatively low, is very suitable for large-scale industrialization
Produce.
For solving above-mentioned technical problem, the technical solution adopted in the present invention is as follows:
The preparation method of a kind of 3-methoxyl group-4-nitrobenzoic acid, comprises the following steps:
First nitrobenzoic acid carry out bromination reaction, and what bromine replaced nitro faces position, by product with
Feldalat NM reacts, and makes bromine by methoxy substitution, obtains target product 3-methoxyl group-4-Nitrobenzol
Formic acid.
As the optimization of technique scheme, the concrete operation method of described course of reaction is: will
Nitrodracylic acid is dissolved in CS2In middle addition reactor, it is added thereto to bromine, controls anti-
Answering still pressure, maintain temperature to react in 30-40 DEG C, after sustained response 2h, it is unnecessary to remove
Br2, and it is added thereto to CH3ONa, at room temperature carries out illumination, is stirred vigorously, holds
After continuous reaction 2h, CS is evaporated off2, the solid obtained is dissolved in the water, filters, will filter out
Solid, rinse, after drying, obtain 3-methoxyl group-4-nitrobenzoic acid.
As the optimization of technique scheme, the molal quantity of described Nitrodracylic acid and CS2
Volume ratio be 0.03-0.05mol/L.
As the optimization of technique scheme, described Nitrodracylic acid with the mol ratio of bromine is
1:1.5-2。
As the optimization of technique scheme, described Nitrodracylic acid and CH3ONa mole
Ratio is 1:2-3.
As the optimization of technique scheme, the pressure of described reactor is 0.8-1.2Mpa.
The method have the advantages that
The nitro utilized and the Orientation Effect of Substituting Groups of carboxyl, make bromine instead of facing of nitro
Position, by-product is less in the process, and polarization is preferable.Nitro and carboxyl is utilized to inhale afterwards
Electronics and give characteristic electron so that it is can react with the Feldalat NM of simple in construction, thus prepared
3-methoxyl group-4-the nitrobenzoic acid that purity is higher, improves the productivity of product simultaneously.Simultaneously
The course of reaction of this programme is simple to operate, and the requirement to condition is gentle, with low cost, the suitableeest
Close large-scale industrial production.
Detailed description of the invention:
In order to be better understood from the present invention, below by embodiment, the present invention is further described,
Embodiment is served only for explaining the present invention, and the present invention will not constitute any restriction.
Embodiment 1
1mol Nitrodracylic acid is dissolved in 20L CS2In middle addition reactor, add wherein
Entering 2mol bromine, controlling reactor pressure is 0.8MPa, maintains temperature to react in 35 DEG C,
After sustained response 2h, remove unnecessary Br2, and it is added thereto to 3mol CH3ONa,
Carry out illumination under room temperature, be stirred vigorously, after sustained response 2h, CS is evaporated off2, by consolidating of obtaining
Body is dissolved in the water, and filters, the solid that will filter out, and rinses, after drying, obtains 3-first
Epoxide-4-nitrobenzoic acid.
The purity of the 3-methoxyl group-4-nitrobenzoic acid of output is 80.2%, and productivity is 85.7%.
Embodiment 2
1mol Nitrodracylic acid is dissolved in 22L CS2In middle addition reactor, add wherein
Entering 1.9mol bromine, controlling reactor pressure is 1.0MPa, maintains temperature to react in 30 DEG C,
After sustained response 2h, remove unnecessary Br2, and it is added thereto to 2.8mol CH3ONa,
Carry out illumination under room temperature, be stirred vigorously, after sustained response 2h, CS is evaporated off2, by consolidating of obtaining
Body is dissolved in the water, and filters, the solid that will filter out, and rinses, after drying, obtains 3-first
Epoxide-4-nitrobenzoic acid.
The purity of the 3-methoxyl group-4-nitrobenzoic acid of output is 82.7%, and productivity is 86.9%.
Embodiment 3
1mol Nitrodracylic acid is dissolved in 25L CS2In middle addition reactor, add wherein
Entering 1.8mol bromine, controlling reactor pressure is 1.2MPa, maintains temperature to react in 40 DEG C,
After sustained response 2h, remove unnecessary Br2, and it is added thereto to 2.5mol CH3ONa,
Carry out illumination under room temperature, be stirred vigorously, after sustained response 2h, CS is evaporated off2, by consolidating of obtaining
Body is dissolved in the water, and filters, the solid that will filter out, and rinses, after drying, obtains 3-first
Epoxide-4-nitrobenzoic acid.
The purity of the 3-methoxyl group-4-nitrobenzoic acid of output is 85.7%, and productivity is 88.4%.
Embodiment 4
1mol Nitrodracylic acid is dissolved in 27L CS2In middle addition reactor, add wherein
Entering 1.7mol bromine, controlling reactor pressure is 1.2MPa, maintains temperature to react in 35 DEG C,
After sustained response 2h, remove unnecessary Br2, and it is added thereto to 2.2mol CH3ONa,
Carry out illumination under room temperature, be stirred vigorously, after sustained response 2h, CS is evaporated off2, by consolidating of obtaining
Body is dissolved in the water, and filters, the solid that will filter out, and rinses, after drying, obtains 3-first
Epoxide-4-nitrobenzoic acid.
The purity of the 3-methoxyl group-4-nitrobenzoic acid of output is 88.3%, and productivity is 84.8%.
Embodiment 5
1mol Nitrodracylic acid is dissolved in 30L CS2In middle addition reactor, add wherein
Entering 1.5mol bromine, controlling reactor pressure is 1.0MPa, maintains temperature to react in 40 DEG C,
After sustained response 2h, remove unnecessary Br2, and it is added thereto to 2mol CH3ONa,
Carry out illumination under room temperature, be stirred vigorously, after sustained response 2h, CS is evaporated off2, by consolidating of obtaining
Body is dissolved in the water, and filters, the solid that will filter out, and rinses, after drying, obtains 3-first
Epoxide-4-nitrobenzoic acid.
The purity of the 3-methoxyl group-4-nitrobenzoic acid of output is 82.7%, and productivity is 85.9%.
It can thus be seen that production method of the present invention, simple to operate, productivity is higher,
It is suitable for large-scale commercial production.
Claims (7)
1. the preparation method of a 3-methoxyl group-4-nitrobenzoic acid, it is characterised in that include
Following steps:
First Nitrodracylic acid carry out bromination reaction, and what bromine replaced nitro faces position, by product
React with Feldalat NM, make bromine by methoxy substitution, obtain target product 3-methoxyl group-4-nitro
Benzoic acid.
The preparation method of 3-methoxyl group-4-nitrobenzoic acid the most according to claim 1,
It is characterized in that, the concrete operation method of described course of reaction is: dissolved by Nitrodracylic acid
In CS2In middle addition reactor, it is added thereto to bromine, controls reactor pressure, maintain temperature
Degree reacts in 30-40 DEG C, after sustained response 2h, removes unnecessary Br2, and add wherein
Enter CH3ONa, at room temperature carries out illumination, is stirred vigorously, after sustained response 2h, be evaporated off
CS2, the solid obtained is dissolved in the water, filters, the solid that will filter out, rinse, dry
After dry, obtain 3-methoxyl group-4-nitrobenzoic acid.
The preparation method of 3-methoxyl group-4-nitrobenzoic acid the most according to claim 2,
It is characterized in that, the molal quantity of described Nitrodracylic acid and CS2Volume ratio be 0.03-0.05
mol/L。
The preparation method of 3-methoxyl group-4-nitrobenzoic acid the most according to claim 2,
It is characterized in that, described Nitrodracylic acid is 1:1.5-2 with the mol ratio of bromine.
The preparation method of 3-methoxyl group-4-nitrobenzoic acid the most according to claim 2,
It is characterized in that, described Nitrodracylic acid and CH3The mol ratio of ONa is 1:2-3.
The preparation method of 3-methoxyl group-4-nitrobenzoic acid the most according to claim 2,
It is characterized in that, the pressure of described reactor is 0.8-1.2Mpa.
7. a kind of 3-methoxyl group-4-nitrobenzoic acid according to any one of claim 1-6
Preparation method preparation-obtained 3-methoxyl group-4-nitrobenzoic acid.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201610171900.1A CN105732394A (en) | 2016-03-23 | 2016-03-23 | 3-methoxy-4-nitrobenzoic acid and preparation method thereof |
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002047287A (en) * | 2000-05-25 | 2002-02-12 | Kyowa Hakko Kogyo Co Ltd | Aromatic derivative |
| CN101563314A (en) * | 2006-12-21 | 2009-10-21 | 纳幕尔杜邦公司 | Process for the synthesis of ethers of aromatic acids |
-
2016
- 2016-03-23 CN CN201610171900.1A patent/CN105732394A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002047287A (en) * | 2000-05-25 | 2002-02-12 | Kyowa Hakko Kogyo Co Ltd | Aromatic derivative |
| CN101563314A (en) * | 2006-12-21 | 2009-10-21 | 纳幕尔杜邦公司 | Process for the synthesis of ethers of aromatic acids |
Non-Patent Citations (5)
| Title |
|---|
| ALEX SHAGINIAN ETAL: "Design, Synthesis, and Evaluation of an r-Helix Mimetic Library Targeting Protein-Protein Interactions", 《J. AM. CHEM. SOC.》 * |
| HAJDU, E.ETAL: "Chloromycetin derivatives. I. The synthesis of 3-bromo-4-nitroacetophenone", 《BIOLOGIE》 * |
| KERSTIN KNEPPER ETAL: "Bartoli Indole Synthesis on Solid Supports", 《ORGANIC LETTERS》 * |
| RIEGER, MARTIN ETAL: "The preparation and resolution of 2,2"-diiodo-5,5"-dicarboxybiphenyl and of 2,2",3,3"-tetraiodo-5,5"-dicarboxybiphenyl", 《JOURNAL OF THE AMERICAN CHEMICAL SOCIETY》 * |
| WILLIAM BLACKBURN ETAL: "The Preparation of 3-Methyl-6- and -7-carboxy-2-quinoxalones", 《JOURNAL OF ORGANIC CHEMISTRY》 * |
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