CN101885670A - Synthesis method of m-phenoxytoluene - Google Patents
Synthesis method of m-phenoxytoluene Download PDFInfo
- Publication number
- CN101885670A CN101885670A CN 201010234546 CN201010234546A CN101885670A CN 101885670 A CN101885670 A CN 101885670A CN 201010234546 CN201010234546 CN 201010234546 CN 201010234546 A CN201010234546 A CN 201010234546A CN 101885670 A CN101885670 A CN 101885670A
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- China
- Prior art keywords
- chlorotoluene
- phenoxytoluene
- synthesis method
- cuprous chloride
- mass ratio
- Prior art date
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Abstract
The invention discloses a synthesis method of m-phenoxytoluene, relating to a synthesis method of a compound. The synthesis method comprises the following steps of: stirring and mixing m-chlorotoluene, sodium phenate, cuprous chloride, 8-oxyquinoline and polydiglycol in a reaction container at the room temperature, heating until the temperature of mixed liquor is 130-140 DEG C and then reacting for 8-9 hours under thermal-insulation stirring; finally, carrying out high-vacuum reduced pressure distillation and getting 100-110 DEG C of distillates to obtain the m-phenoxytoluene. In the invention, under the catalytic action of the cuprous chloride, the 8-oxyquinoline and the polydiglycol, the sodium phenate and the m-chlorotoluene are directly taken as raw materials to carry out single-step reaction to prepare the m-phenoxytoluene, wherein the m-chlorotoluene is a reactant and meanwhile takes the solvent action so that any solvent does not need to be additionally used, thereby greatly reducing cost.
Description
Technical field
The present invention relates to the synthetic method of a compounds, particularly the synthetic method of m-phenoxytoluene and analogue thereof.
Background technology
M-phenoxytoluene is a class important chemical intermediate, has application widely aspect chemical materials, medication chemistry and the meticulous organic chemical industry.
The synthetic method of existing meta-methoxy toluene compounds all adopts sodium phenylate to react laggard one-step removal electron withdrawing group with the m-chlorotoluene with electron withdrawing group replacement under cuprous chloride catalysis and obtains.Such reaction relates to the introducing of electron withdrawing group and removes step and cause the long and not high shortcoming of overall yield of step.Simultaneously the catalyzer cuprous chloride is a heterogeneous catalyst in this reaction, and catalytic effect is unsatisfactory, and when running into the m-chlorotoluene that does not contain electron withdrawing group and being raw material, this reaction can not take place.
Therefore, seeking a kind of is that method that the raw material single step reaction obtains m-phenoxytoluene is an industrial technical barrier that needs to be resolved hurrily at present with sodium phenylate and m-chlorotoluene directly.
Summary of the invention
Purpose of the present invention just is to overcome the above-mentioned defective of existing production technology, develop a kind of efficiently, the synthetic method of m-phenoxytoluene compounds easily.
Technical solution of the present invention is: m-chlorotoluene, sodium phenylate, cuprous chloride, oxine and poly-glycol ether stirring at normal temperature in reaction vessel is mixed, and the temperature that is heated to mixed solution is 130～140 ℃ that the insulated and stirred reaction is 8～9 hours then; After 100～110 ℃ fraction is got in the high vacuum underpressure distillation, promptly get m-phenoxytoluene.
The present invention is a catalyzer with cuprous chloride, oxine and poly-glycol ether, such composite catalyst has extraordinary catalytic activity for the m-chlorotoluene that non-electron withdrawing group replaces, and the present invention is that the raw material single step reaction makes m-phenoxytoluene with sodium phenylate and m-chlorotoluene directly; If what add is the sodium phenylate of various different substituents, then can obtain the various different m-phenoxytoluene molecules that replace.The present invention does not need additionally to use any solvent, and m-chlorotoluene is a reactant, plays the effect of solvent simultaneously again, greatly reduces cost like this.
In order to save raw materials for production, the mass ratio that feeds intake of m-chlorotoluene of the present invention and sodium phenylate is 5.0～5.5: 1.
The mass ratio that feeds intake of described m-chlorotoluene and cuprous chloride is 3～3.2: 1.
The mass ratio that feeds intake of described m-chlorotoluene and oxine is 30～32: 1.
The mass ratio that feeds intake of described m-chlorotoluene and poly-glycol ether is 30～32: 1.
Embodiment
Concrete reaction formula of the present invention is:
In the formula,
The poly-glycol ether of expression, the polymerization degree can play catalytic effect arbitrarily.Reaction conditions is heating.This reaction equation is represented: the sodium phenylate that is applicable to the difference replacement of this method.
Concrete steps are as follows:
1, m-chlorotoluene 126.5g, sodium phenylate 23.2g, cuprous chloride 42g, oxine 4.1g, poly-glycol ether 4.0g are dropped in the 500mL round-bottomed flask stirring at normal temperature 5 ± 1 minutes respectively;
2, will be heated to 130～140 ℃ under the mixed solution whipped state;
3, with mixed solution 130～140 ℃ of following insulated and stirred 8～9 hours;
4, after reaction finishes, and the high vacuum underpressure distillation (14～16mmHg), get 100～110 ℃ fraction, can obtain final compound.
Claims (5)
1. the synthetic method of m-phenoxytoluene, it is characterized in that: m-chlorotoluene, sodium phenylate, cuprous chloride, oxine and poly-glycol ether stirring at normal temperature in reaction vessel is mixed, and the temperature that is heated to mixed solution is 130～140 ℃, and the insulated and stirred reaction is 8～9 hours then; After 100～110 ℃ fraction is got in the high vacuum underpressure distillation, promptly get m-phenoxytoluene.
2. according to the described method of claim 1, it is characterized in that the mass ratio that feeds intake of described m-chlorotoluene and sodium phenylate is 5.0～5.5: 1.
3. according to the described method of claim 1, it is characterized in that the mass ratio that feeds intake of described m-chlorotoluene and cuprous chloride is 3～3.2: 1.
4. according to the described method of claim 1, it is characterized in that the mass ratio that feeds intake of described m-chlorotoluene and oxine is 30～32: 1.
5. method according to claim 1 is characterized in that the mass ratio that feeds intake of described m-chlorotoluene and poly-glycol ether is 30～32: 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 201010234546 CN101885670A (en) | 2010-07-19 | 2010-07-19 | Synthesis method of m-phenoxytoluene |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 201010234546 CN101885670A (en) | 2010-07-19 | 2010-07-19 | Synthesis method of m-phenoxytoluene |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN101885670A true CN101885670A (en) | 2010-11-17 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 201010234546 Pending CN101885670A (en) | 2010-07-19 | 2010-07-19 | Synthesis method of m-phenoxytoluene |
Country Status (1)
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| CN (1) | CN101885670A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107428704A (en) * | 2015-10-06 | 2017-12-01 | Gsp作物科学有限公司 | The method for preparing Fluoxastrobin |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4288386A (en) * | 1979-05-18 | 1981-09-08 | Rhone-Poulenc Industries | Ullmann reaction for the synthesis of diaryl ethers |
| JPS59134743A (en) * | 1983-01-24 | 1984-08-02 | Toray Ind Inc | Preparation of m-phenoxytoluene |
| US4564712A (en) * | 1980-10-30 | 1986-01-14 | Hoechst Aktiengesellschaft | Process for the preparation of diphenyl ethers |
-
2010
- 2010-07-19 CN CN 201010234546 patent/CN101885670A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4288386A (en) * | 1979-05-18 | 1981-09-08 | Rhone-Poulenc Industries | Ullmann reaction for the synthesis of diaryl ethers |
| US4564712A (en) * | 1980-10-30 | 1986-01-14 | Hoechst Aktiengesellschaft | Process for the preparation of diphenyl ethers |
| JPS59134743A (en) * | 1983-01-24 | 1984-08-02 | Toray Ind Inc | Preparation of m-phenoxytoluene |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107428704A (en) * | 2015-10-06 | 2017-12-01 | Gsp作物科学有限公司 | The method for preparing Fluoxastrobin |
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Application publication date: 20101117 |