CN104058956A - Production process for synthesizing 3-bromo-2, 6-dimethoxybenzoic acid - Google Patents
Production process for synthesizing 3-bromo-2, 6-dimethoxybenzoic acid Download PDFInfo
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- CN104058956A CN104058956A CN201410244907.2A CN201410244907A CN104058956A CN 104058956 A CN104058956 A CN 104058956A CN 201410244907 A CN201410244907 A CN 201410244907A CN 104058956 A CN104058956 A CN 104058956A
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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
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/363—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/09—Preparation of ethers by dehydration of compounds containing hydroxy groups
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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
- C07C51/15—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction of organic compounds with carbon dioxide, e.g. Kolbe-Schmitt synthesis
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Abstract
The invention discloses a production process for synthesizing 3-bromo-2, 6-dimethoxybenzoic acid, relating to the technical field of chemical industry. The preparation process comprises the steps of preparing 2, 6-dimethoxybenzoic acid through synthesizing 2-bromo-m-dimethoxybenzene; then, preparing 3-bromo-2, 6-dimethoxybenzoic acid by taking 2, 6-dimethoxybenzoic acid as a raw material. The production process has the beneficial effects of convenience and simplicity in preparation, environment friendliness, easily-obtained raw materials, low equipment investment, high purity and convenience in operation; in addition, the prepared 3-bromo-2, 6-dimethoxybenzoic acid is good in using effect and is safe and reliable.
Description
Technical field
The present invention relates to chemical technology field, be specifically related to the synthetic production technique of bromo-2,6 dimethoxybenzoic acids of 3-.
Background technology
Bromo-2,6 dimethoxybenzoic acids of 3-are white or baby pink crystallization.254.5 ℃ of fusing points, relative density 1.894 (20/4 ℃).Be dissolved in alcohol and ether, be slightly soluble in water, for spices, prepare spices and pharmaceutical industry, also be used as the raw material of sanitas sanitas, medicine and spices, in domestic a lot of organic synthesis, be used widely, in bromo-2,6 dimethoxybenzoic acids of industrial production 3-, have the problems such as yield is low, not high pollution of purity is serious at present, and production technique is comparatively complicated, is difficult to meet human wants.
Summary of the invention
Technical problem to be solved by this invention is to provide a kind of purity high, the production technique that the simple para-bromo toluene of preparation technology is synthetic.
Technical problem to be solved by this invention realizes by the following technical solutions:
The synthetic production technique of bromo-2,6 dimethoxybenzoic acids of 3-, is characterized in that: comprise following processing step,
(1) 2-bromine m-dimethoxybenzene is synthetic
A. choose a reaction flask and within it portion add 180-190g2-bromine Resorcinol, methyl alcohol 190-210ml, methyl-sulfate 125-130g carries out stirring and dissolving.
B. in the reaction flask in step a, add cryosel bath to be chilled to temperature and be-5 ℃, add at once the aqueous solution of 140-160g potassium hydroxide and 340-360g, continue to stir 5min.
C. after reaction in step b finishes, to reaction flask inside, add moisture oil-yielding stratum, water layer ether extraction, merge oil reservoir and organic layer, then washing, is adopting Calcium Chloride Powder Anhydrous to be dried, then filter, it is standby that underpressure distillation obtains 2-bromine m-dimethoxybenzene resulting solution.
(2) 2,6-dimethoxybenzoic acids are synthetic
A. choose a dry reaction flask, in reaction flask, add the magnesium powder of 2.5-3.0g, anhydrous diethyl ether 45-55ml, iodine 0.5-1.5g also stirs.
B. the anhydrous diethyl ether that the 2-bromine m-dimethoxybenzene of system in step () is taken to 21.5-22.0g and 25-35ml is configured to solution, and then heated and stirred is until magnesium chips completely dissolve.
C. adopt cryosel to bathe cooling, in the situation that constantly stirring, pass into dry carbonic acid gas 2.0h.
D. in the mixture in step c, add frozen water 90-110g, then separate organic layer, water layer is with merging organic layer after ether extraction.
E. the organic layer merging in steps d is adopted to 10% sodium hydroxide solution extraction three times, after merging buck layer, adopt again hydrochloric acid that PH is adjusted to 1-2, then use ether extraction 3 times, merge organic layer, adopt Calcium Chloride Powder Anhydrous dry, filter, it is standby that crystallize out obtains 2,6-dimethoxybenzoic acid.
(3) bromo-2,6 dimethoxybenzoic acids of 3-
A. choose reaction flask, in reaction flask, add that 72.5-73.0g step (two) makes 2, the dioxane of 6-dimethoxybenzoic acid, 550-650ml.
B. the continuous mixture in whipping step a, and in the situation that stirring, drip the bromine of 15-25ml and continue stirring 2.0h with the solution of the trichloromethane of 90-110ml preparation.
C. after reaction, reclaim solvent, separate out solid, obtain bromo-2,6 dimethoxybenzoic acids of thick 3-.
D. by dry after bromo-2, the 6 dimethoxybenzoic acids employing ethyl alcohol recrystallizations of the thick 3-in step c, obtain bromo-2, the 6 dimethoxybenzoic acid finished products of 3-, can pack warehouse-in.
The invention has the beneficial effects as follows: the present invention is easy to prepare simple, and environment friendly and pollution-free, raw material is easy to get, and facility investment is few, and purity is high, convenient operation, bromo-2, the 6 dimethoxybenzoic acid results of use of 3-of preparation are good, safe and reliable.
Embodiment
For technique means, creation characteristic that the present invention is realized, reach object and effect is easy to understand, below in conjunction with specific embodiment, further set forth the present invention.
Embodiment 1
The synthetic production technique of bromo-2,6 dimethoxybenzoic acids of 3-, comprises following processing step,
(1) 2-bromine m-dimethoxybenzene is synthetic
A. choose a reaction flask and within it portion add 180g2-bromine Resorcinol, methyl alcohol 190ml, methyl-sulfate 125g carries out stirring and dissolving.
B. in the reaction flask in step a, add cryosel bath to be chilled to temperature and be-5 ℃, add at once the aqueous solution of 140g potassium hydroxide and 340-360g, continue to stir 5min.
C. after reaction in step b finishes, to reaction flask inside, add moisture oil-yielding stratum, water layer ether extraction, merge oil reservoir and organic layer, then washing, is adopting Calcium Chloride Powder Anhydrous to be dried, then filter, it is standby that underpressure distillation obtains 2-bromine m-dimethoxybenzene resulting solution.
(2) 2,6-dimethoxybenzoic acids are synthetic
A. choose a dry reaction flask, in reaction flask, add the magnesium powder of 2.5g, anhydrous diethyl ether 45ml, iodine 0.5g also stirs.
B. the anhydrous diethyl ether that the 2-bromine m-dimethoxybenzene of system in step () is taken to 21.5g and 25ml is configured to solution, and then heated and stirred is until magnesium chips completely dissolve.
C. adopt cryosel to bathe cooling, in the situation that constantly stirring, pass into dry carbonic acid gas 2.0h.
D. in the mixture in step c, add frozen water 90g, then separate organic layer, water layer is with merging organic layer after ether extraction.
E. the organic layer merging in steps d is adopted to 10% sodium hydroxide solution extraction three times, after merging buck layer, adopt again hydrochloric acid that PH is adjusted to 1, then use ether extraction 3 times, merge organic layer, adopt Calcium Chloride Powder Anhydrous dry, filter, it is standby that crystallize out obtains 2,6-dimethoxybenzoic acid.
(3) bromo-2,6 dimethoxybenzoic acids of 3-
A. choose reaction flask, in reaction flask, add that 72.5g step (two) makes 2, the dioxane of 6-dimethoxybenzoic acid, 550ml.
B. the continuous mixture in whipping step a, and in the situation that stirring, drip the bromine of 15ml and continue stirring 2.0h with the solution of the trichloromethane of 90ml preparation.
C. after reaction, reclaim solvent, separate out solid, obtain bromo-2,6 dimethoxybenzoic acids of thick 3-.
D. by dry after bromo-2, the 6 dimethoxybenzoic acids employing ethyl alcohol recrystallizations of the thick 3-in step c, obtain bromo-2, the 6 dimethoxybenzoic acid finished products of 3-, can pack warehouse-in.
Embodiment 2
The synthetic production technique of bromo-2,6 dimethoxybenzoic acids of 3-, is characterized in that: comprise following processing step,
(1) 2-bromine m-dimethoxybenzene is synthetic
A. choose a reaction flask and within it portion add 189g2-bromine Resorcinol, methyl alcohol 200ml, methyl-sulfate 126g carries out stirring and dissolving.
B. in the reaction flask in step a, add cryosel bath to be chilled to temperature and be-5 ℃, add at once the aqueous solution of 150g potassium hydroxide and 350g, continue to stir 5min.
C. after reaction in step b finishes, to reaction flask inside, add moisture oil-yielding stratum, water layer ether extraction, merge oil reservoir and organic layer, then washing, is adopting Calcium Chloride Powder Anhydrous to be dried, then filter, it is standby that underpressure distillation obtains 2-bromine m-dimethoxybenzene resulting solution.
(2) 2,6-dimethoxybenzoic acids are synthetic
A. choose a dry reaction flask, in reaction flask, add the magnesium powder of 2.6g, anhydrous diethyl ether 50ml, iodine 1.0g also stirs.
B. the anhydrous diethyl ether that the 2-bromine m-dimethoxybenzene of system in step () is taken to 21.7g and 30ml is configured to solution, and then heated and stirred is until magnesium chips completely dissolve.
C. adopt cryosel to bathe cooling, in the situation that constantly stirring, pass into dry carbonic acid gas 2.0h.
D. in the mixture in step c, add frozen water 100g, then separate organic layer, water layer is with merging organic layer after ether extraction.
E. the organic layer merging in steps d is adopted to 10% sodium hydroxide solution extraction three times, after merging buck layer, adopt again hydrochloric acid that PH is adjusted to 2, then use ether extraction 3 times, merge organic layer, adopt Calcium Chloride Powder Anhydrous dry, filter, it is standby that crystallize out obtains 2,6-dimethoxybenzoic acid.
(3) bromo-2,6 dimethoxybenzoic acids of 3-
A. choose reaction flask, in reaction flask, add that 72.8g step (two) makes 2, the dioxane of 6-dimethoxybenzoic acid, 600ml.
B. the continuous mixture in whipping step a, and in the situation that stirring, drip the bromine of 20ml and continue stirring 2.0h with the solution of the trichloromethane of 100ml preparation.
C. after reaction, reclaim solvent, separate out solid, obtain bromo-2,6 dimethoxybenzoic acids of thick 3-.
D. by dry after bromo-2, the 6 dimethoxybenzoic acids employing ethyl alcohol recrystallizations of the thick 3-in step c, obtain bromo-2, the 6 dimethoxybenzoic acid finished products of 3-, can pack warehouse-in.
More than show and described ultimate principle of the present invention and principal character and advantage of the present invention.The technician of the industry should understand; the present invention is not restricted to the described embodiments; that in above-described embodiment and specification sheets, describes just illustrates principle of the present invention; without departing from the spirit and scope of the present invention; the present invention also has various changes and modifications, and these changes and improvements all fall in the claimed scope of the invention.The claimed scope of the present invention is defined by appending claims and equivalent thereof.
Claims (1)
- The synthetic production technique of bromo-2,6 dimethoxybenzoic acids of 1.3-, is characterized in that: comprise following processing step,(1) 2-bromine m-dimethoxybenzene is syntheticA. choose a reaction flask and within it portion add 180-190g2-bromine Resorcinol, methyl alcohol 190-210ml, methyl-sulfate 125-130g carries out stirring and dissolving.B. in the reaction flask in step a, add cryosel bath to be chilled to temperature and be-5 ℃, add at once the aqueous solution of 140-160g potassium hydroxide and 340-360g, continue to stir 5min.C. after reaction in step b finishes, to reaction flask inside, add moisture oil-yielding stratum, water layer ether extraction, merge oil reservoir and organic layer, then washing, is adopting Calcium Chloride Powder Anhydrous to be dried, then filter, it is standby that underpressure distillation obtains 2-bromine m-dimethoxybenzene resulting solution.(2) 2,6-dimethoxybenzoic acids are syntheticA. choose a dry reaction flask, in reaction flask, add the magnesium powder of 2.5-3.0g, anhydrous diethyl ether 45-55ml, iodine 0.5-1.5g also stirs.B. the anhydrous diethyl ether that the 2-bromine m-dimethoxybenzene of system in step () is taken to 21.5-22.0g and 25-35ml is configured to solution, and then heated and stirred is until magnesium chips completely dissolve.C. adopt cryosel to bathe cooling, in the situation that constantly stirring, pass into dry carbonic acid gas 2.0h.D. in the mixture in step c, add frozen water 90-110g, then separate organic layer, water layer is with merging organic layer after ether extraction.E. the organic layer merging in steps d is adopted to 10% sodium hydroxide solution extraction three times, after merging buck layer, adopt again hydrochloric acid that PH is adjusted to 1-2, then use ether extraction 3 times, merge organic layer, adopt Calcium Chloride Powder Anhydrous dry, filter, it is standby that crystallize out obtains 2,6-dimethoxybenzoic acid.(3) bromo-2,6 dimethoxybenzoic acids of 3-A. choose reaction flask, in reaction flask, add that 72.5-73.0g step (two) makes 2, the dioxane of 6-dimethoxybenzoic acid, 550-650ml.B. the continuous mixture in whipping step a, and in the situation that stirring, drip the bromine of 15-25ml and continue stirring 2.0h with the solution of the trichloromethane of 90-110ml preparation.C. after reaction, reclaim solvent, separate out solid, obtain bromo-2,6 dimethoxybenzoic acids of thick 3-.D. by dry after bromo-2, the 6 dimethoxybenzoic acids employing ethyl alcohol recrystallizations of the thick 3-in step c, obtain bromo-2, the 6 dimethoxybenzoic acid finished products of 3-, can pack warehouse-in.
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4232037A (en) * | 1978-03-23 | 1980-11-04 | Astra Lakemedel Aktiebolag | 2,6-Dialkoxybenzamides, intermediates, pharamaceutical compositions and methods for treatment of psychotic disorders |
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2014
- 2014-06-04 CN CN201410244907.2A patent/CN104058956A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4232037A (en) * | 1978-03-23 | 1980-11-04 | Astra Lakemedel Aktiebolag | 2,6-Dialkoxybenzamides, intermediates, pharamaceutical compositions and methods for treatment of psychotic disorders |
Non-Patent Citations (2)
| Title |
|---|
| 吉民等: ""抗精神***症药瑞莫必利的合成"", 《中国药科大学学报》 * |
| 蔡孟深等: ""碳苷研究Ⅴ.用Grignard试剂合成取代苯酚中酚羟基的保护及脱保护"", 《化学学报》 * |
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Application publication date: 20140924 |