CN104672062A - Synthetic method of 2, 3, 5-trimethylphenol - Google Patents
Synthetic method of 2, 3, 5-trimethylphenol Download PDFInfo
- Publication number
- CN104672062A CN104672062A CN201310639314.1A CN201310639314A CN104672062A CN 104672062 A CN104672062 A CN 104672062A CN 201310639314 A CN201310639314 A CN 201310639314A CN 104672062 A CN104672062 A CN 104672062A
- Authority
- CN
- China
- Prior art keywords
- synthetic method
- tep
- grams
- reaction
- tmp
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a synthetic method of 2, 3, 5-trimethylphenol and belongs to the technical field of chemical synthesis. The synthetic method is characterized by comprising the following steps: with 2, 3, 6-trimethylphenol as a raw material, carrying out rearrangement reaction under the action of aluminum trihalide to prepare the 2, 3, 5-trimethylphenol. The synthetic method has the advantages of easiness in raw material acquisition, simpleness in operation, mildness in reaction condition, high synthesis yield, good quality and the like and is suitable for industrial production.
Description
Technical field:
The invention belongs to chemosynthesis technical field, specifically, relate to a kind of synthetic method of 2,3,5-TEP.
Background technology:
2,3,5-TEP is the important source material of synthetic aroma tretinoin, A Quting, trimethacarb etc., and also may be used for synthesising complex E main ring TMHQ, is a kind of important medicine, pesticide intermediate.
The synthetic method of current 2,3,5-TEP is mainly raw material with MX, in the presence of a catalyst, reacts, obtain 2,3,5-TEP with methyl alcohol.The method application is comparatively extensive, but exists obviously not enough, and mainly reaction conditions is harsher, and there is many methylated by-product, yield has much room for improvement.In addition, also have bibliographical information, separating-purifying 2,3,5-TEP from phenol slag, but due to phenol slag source instability, quality is uneven, therefore cannot meet the requirement of industrial mass production and stable product quality.
Summary of the invention:
A first aspect of the present invention object is to provide a kind of raw material to be easy to get, simple to operate, the synthetic method of the 2,3,5-TEP of reaction conditions gentleness.
The technical solution used in the present invention is as follows:
A synthetic method for 2,3,5-TEP, is characterized in that: take 2,3,6-TMP as raw material, under aluminum trihalide effect, through rearrangement reaction, prepares 2,3,5-TEP.
The synthetic route that the present invention adopts can represent with following reaction formula:
Further, under following preferred reaction conditions, better yield can be obtained, and the 2,3,5-TEP of more high product quality (purity reaches more than 99%).
Described aluminum trihalide be selected from following one or both: aluminum chloride, alchlor, aluminum trihalide with the ratio of the amount of substance of 2,3,6-TMP is: 1:1 ~ 3:1.
In reaction process, add appropriate anhydrous hydrogen halide, promote reaction carrying out, described hydrogen halide be selected from following one or both: hydrogenchloride, hydrogen bromide.Hydrogen halide with the ratio of the amount of substance of 2,3,6-TMP is: 0.1:1 ~ 20:1.Hydrogen halide can adopt the mode of bubbling, continues to add in reaction process, also can adopt the front disposable method passed into of reaction.Using airtight reaction system, maintenance system pressure after hydrogen halide passes into, is ensure to there are one of effective ways of enough hydrogen halide in reaction system.
Reaction can be carried out under solvent-free, preferably carry out in presence of organic solvent, organic solvent be selected from following one or more: normal hexane, normal heptane, octane, hexanaphthene, benzene,toluene,xylene, solvent load is 2,1 ~ 10 times of 3,6-pseudocuminol quality.
Temperature of reaction controls 90 ~ 170 DEG C time, and yield is best.
Compared with prior art, its useful effect is embodied in: raw material is easy to get, simple to operate in the present invention, and reaction conditions is gentle, and synthesis yield is high, good product quality, is applicable to suitability for industrialized production.
Below in conjunction with embodiment, the invention will be further described.
Embodiment:
Embodiment one:
In 250 milliliters of three mouthfuls of reaction flasks, add 2,3,6-TMP 68 grams, dimethylbenzene 68 grams, stirring and dissolving, add aluminum trichloride (anhydrous) 166 grams in batches, system is warming up to 130 DEG C of reactions 5 hours.Reaction system is cooled to 50 DEG C, is slowly diluted in 200 grams of water, separates organic phase, and aqueous phase 50 grams of xylene extraction 1 time, merge organic phase, with 50 grams of water washings, and anhydrous sodium sulfate drying.Cross and filter sodium sulfate, filtrate reduced in volume to system in the pasty state, stop concentrated, residue filters, and filter cake is drained, and obtains 2,3,5-TEP 55 grams, purity 99.3%.
Embodiment two:
In 250 milliliters of three mouthfuls of reaction flasks, add 2,3,6-TMP 68 grams, anhydrous alchlor 160 grams, system is slowly warming up to 160 DEG C of reactions 3 hours.Reaction system be diluted in 400 grams of water, after dilution, add ethyl acetate 200 grams, stir, separate organic phase, aqueous phase ethyl acetate 50 grams extraction 1 time, merges organic phase, with 50 grams of water washings, and anhydrous sodium sulfate drying.Filter, filtrate reduced in volume, adds hexanaphthene 50 grams in residue, stirring at room temperature 30 minutes, and filter, filter cake is drained, and obtains 2,3,5-TEP 53 grams, purity 99.1%.
Embodiment three:
In 500 milliliters of three mouthfuls of reaction flasks, add 2,3,6-pseudocuminol 150 grams, stirring is warming up to 100 DEG C and adds aluminum trichloride (anhydrous) 294 grams in batches, and reaction system was in 100 DEG C of reactions 6 hours, reaction system is slowly diluted in 400 grams of water, after dilution, adds toluene 300 grams, stir, separate organic phase, aqueous phase 100 grams of toluene extract 1 time, merge organic phase, with 50 grams of water washings, anhydrous sodium sulfate drying.Filter, filtrate reduced in volume, to system pasty state, stop concentrated, residue filters, and filter cake is drained, and obtains 2,3,5-TEP 128 grams, purity 99.4%.
Embodiment four:
In 500 milliliters of autoclaves, add 2,3,6-pseudocuminol 50 grams, hexanaphthene 150 grams, aluminum trichloride (anhydrous) 74 grams, enclosed high pressure still, passes into dry hydrogen chloride gas 70 grams, and system stirs and is warming up to 110 DEG C of reactions 5 hours, reaction system is diluted in 200 grams of water, separate organic phase, aqueous phase with 100 grams of extraction into ethyl acetate once, merge organic phase, with 50 grams of water washings, anhydrous sodium sulfate drying.Filter, filtrate reduced in volume, adds normal hexane 50 grams in residue, stirring at room temperature 30 minutes, and filter, filter cake is drained, and obtains 2,3,5-TEP 46 grams, purity 98.7%.
Claims (7)
1. a synthetic method for 2,3,5-TEP, is characterized in that: take 2,3,6-TMP as raw material, under aluminum trihalide effect, through rearrangement reaction, prepare 2,3,5-TEP.
2. the synthetic method of a kind of 2,3,5-TEP according to claim 1, it is characterized in that: described aluminum trihalide be selected from following one or both: aluminum chloride, alchlor, aluminum trihalide with the ratio of the amount of substance of 2,3,6-TMP is: 1:1 ~ 3:1.
3. the synthetic method of a kind of 2,3,5-TEP according to claim 1, is characterized in that: in reaction process, adds anhydrous hydrogen halide, promotes that reaction is carried out.
4. the synthetic method of a kind of 2,3,5-TEP according to claim 1 or 3, it is characterized in that: hydrogen halide be selected from following one or both: hydrogenchloride, hydrogen bromide, hydrogen halide with the ratio of the amount of substance of 2,3,6-TMP is: 0.1:1 ~ 20:1.
5. the synthetic method of a kind of 2,3,5-TEP according to claim 1, is characterized in that: react and carry out under solvent-free, or carry out in the presence of an organic.
6. according to claim 5 a kind of 2,3, the synthetic method of 5-pseudocuminol, it is characterized in that: described organic solvent be selected from following one or more: normal hexane, normal heptane, octane, hexanaphthene, benzene,toluene,xylene, solvent load is 2,1 ~ 10 times of 3,6-pseudocuminol quality.
7. the synthetic method of a kind of 2,3,5-TEP according to claim 1, is characterized in that: temperature of reaction is 90 ~ 170
oc.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310639314.1A CN104672062A (en) | 2013-12-02 | 2013-12-02 | Synthetic method of 2, 3, 5-trimethylphenol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310639314.1A CN104672062A (en) | 2013-12-02 | 2013-12-02 | Synthetic method of 2, 3, 5-trimethylphenol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN104672062A true CN104672062A (en) | 2015-06-03 |
Family
ID=53307713
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201310639314.1A Pending CN104672062A (en) | 2013-12-02 | 2013-12-02 | Synthetic method of 2, 3, 5-trimethylphenol |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN104672062A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109251132A (en) * | 2018-10-18 | 2019-01-22 | 西北化工研究院有限公司 | A kind of method that 2,6- xylenol isomery is combined to high added value xylenol |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1112502A (en) * | 1966-04-22 | 1968-05-08 | Coalite Chem Prod Ltd | Rearrangement of xylenols |
| US4503270A (en) * | 1983-11-21 | 1985-03-05 | General Electric Company | Method of producing 2,3,6 trimethylphenol |
-
2013
- 2013-12-02 CN CN201310639314.1A patent/CN104672062A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1112502A (en) * | 1966-04-22 | 1968-05-08 | Coalite Chem Prod Ltd | Rearrangement of xylenols |
| US4503270A (en) * | 1983-11-21 | 1985-03-05 | General Electric Company | Method of producing 2,3,6 trimethylphenol |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109251132A (en) * | 2018-10-18 | 2019-01-22 | 西北化工研究院有限公司 | A kind of method that 2,6- xylenol isomery is combined to high added value xylenol |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN106928055A (en) | A kind of method that use choline eutectic solvent catalyzes and synthesizes aspirin | |
| CN102391128B (en) | Production method of antibiotic pharmaceutical intermediate mono-p-nitro benzyl malonate | |
| CN104672062A (en) | Synthetic method of 2, 3, 5-trimethylphenol | |
| CN109096354A (en) | A kind of testosterone intermediate mother liquor recycling method | |
| CN103254265A (en) | Abiraterone acetate trifluoroacetate, and preparation method and application thereof | |
| CN103172499B (en) | Oxyresveratrol synthesis method | |
| CN103214534A (en) | Preparation method of 3'-desoxyadenossine | |
| CN104725460B (en) | Male steroid-4-alkene-6 ��, the preparation method of 19-ring oxygen-3,17-diketone | |
| CN104402849B (en) | The new preparation process of Ta Simeiqiong intermediate | |
| CN102532195B (en) | Method for synthesis of chlorpyrifos | |
| EP3181576A1 (en) | Method for synthesizing 25-hydroxy cholesterol | |
| CN104693025A (en) | Feeding manner for preparing L-monomenthyl glutarate | |
| CN104356103A (en) | Synthetic method of 6, 7-dimethoxyl coumarin | |
| CN103804342A (en) | Preparation method for piperonyl acetate | |
| CN105367477B (en) | A method of synthesis 1- methyl tryptophan | |
| CN102977140A (en) | Multiple composite catalyst-induced chlorpyrifos preparation method | |
| CN103848879A (en) | Method for preparing progesterone by taking 1,4-androstenedione as raw material | |
| CN103408457A (en) | Synthetic method of butanedione monoxime sodium and potassium salt | |
| CN103012461B (en) | Preparation method of biotin key intermediate 1, 2-bi(trimethylsilanolate) cyclohexene | |
| CN102850384A (en) | Synthesizing of 4-chloro-7-methoxyindole-2-boric acid | |
| CN101891569B (en) | Preparation method of alpha-aromatic ketone compound | |
| CN105440094A (en) | Preparation method of dexamethasone intermediate | |
| CN104130297A (en) | Method for synthesizing capecitabine key intermediate by using high-efficiency dehydrating agent | |
| CN103896834A (en) | 2-Cyano-3-cyclobutylpyridine and chemical synthesis method thereof | |
| CN103044345B (en) | A kind of synthetic method of 1-(2-hydroxyethyl)-5-sulfydryl-1H-tetrazole |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| CB02 | Change of applicant information |
Address after: 312000 Hangzhou Bay Shangyu economic and Technological Development Zone, Zhejiang, Shaoxing Applicant after: ZHEJIANG ZHONGXIN FLUORINE MATERIALS CO., LTD. Address before: 312000 Zhejiang city of Shaoxing province Shangyu city Hangzhou Bay Industrial Park, Shangyu Road No. 2 Applicant before: Zhejiang Zhongxin Chemical Co., Ltd. |
|
| COR | Change of bibliographic data | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20150603 |
|
| RJ01 | Rejection of invention patent application after publication |