CN105566172A - Synthetic method of selective methylation reagent methyl p-toluenesulfonate - Google Patents
Synthetic method of selective methylation reagent methyl p-toluenesulfonate Download PDFInfo
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- CN105566172A CN105566172A CN201510976362.9A CN201510976362A CN105566172A CN 105566172 A CN105566172 A CN 105566172A CN 201510976362 A CN201510976362 A CN 201510976362A CN 105566172 A CN105566172 A CN 105566172A
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- methylation reagent
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- methyl tosylate
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/26—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids
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Abstract
Disclosed is a synthetic method of selective methylation reagent methyl p-toluenesulfonate. The synthetic method is characterized by including the following steps: (i) adding 0.271mol of p-toluenesulfonyl bromine (2) into a reaction vessel provided with a stirrer, a temperature gauge and a dropping funnel and 1.57-1.59mol of 2,2,2-trifluoroethyl methyl ether, controlling the stirring rate at 160-190rpm, controlling the solution temperature at 35-40 DEG C, dropwise adding 300ml of potassium carbonate solution with the time of dropwise adding controlled to be 2-3h, maintaining the stirring state for 5-6h after addition, separating an oil layer, sequentially washing with saline solution, sodium sulfite solution and dimethylamine solution, dehydrating with a dehydrating agent, performing reduced pressure distillation, and collecting distillate at the temperature of 140-145 DEG C to obtain methyl p-toluenesulfonate (1), wherein the mass fraction of the potassium carbonate solution is 45-50%, and the saline solution in the step (i) is any one of potassium bromide and sodium chloride.
Description
Technical field
The present invention relates to a kind of synthetic method of selective methylation reagent methyl tosylate.
Background technology
Methyl tosylate is used as the selective methylation reagent of organic synthesis, for the manufacture of dye well organic synthesis, to methylate raw material as preparation, the selective methylation reagent of organic synthesis and catalyzer, therefore, the synthetic method of itself is good and bad for raising pharmaceutical synthesis quality product, reduces by-products content and has Important Economic meaning.
Summary of the invention
The object of the present invention is to provide a kind of synthetic method of selective methylation reagent methyl tosylate, comprise the steps:
I () is being provided with agitator, thermometer, in the reaction vessel of dropping funnel, add tolysulfonyl bromine (2) 0.271mol, 2, 2, 2-trifluoroethyl methyl ether 1.57-1.59mol, control stirring velocity at 160-190rpm, solution temperature controls at 35--40 DEG C, drip solution of potassium carbonate 300ml, time for adding controls at 2-3h, add rear maintenance whipped state 5-6h, divide oil-yielding stratum, use brine successively, sodium sulfite solution washs, dimethylamine solution washs, dewatering agent dewaters, underpressure distillation, collect the cut of 140--145 DEG C, obtain methyl tosylate (1),
Wherein, the massfraction of the solution of potassium carbonate described in step (i) is 45-50%, salts solution described in step (i) is any one in Potassium Bromide, sodium-chlor, the massfraction of the sodium sulfite solution described in step (i) is 30-35%, the massfraction of the dimethylamine solution described in step (i) is 75-80%, dewatering agent described in step (i) is any one in calcium sulfate, activated alumina, underpressure distillation described in step (i), residing pressure is 1.8-1.9kPa.
Whole reaction process can represent with following reaction formula:
The invention has the advantages that: the middle-chain decreasing reaction, reduce temperature of reaction and reaction times, improve reaction yield.
Embodiment
Below in conjunction with concrete embodiment, the invention will be further described:
A kind of synthetic method of selective methylation reagent methyl tosylate
Example 1:
Agitator is being installed, thermometer, in the reaction vessel of dropping funnel, add tolysulfonyl bromine (2) 0.271mol, 2, 2, 2-trifluoroethyl methyl ether 1.57mol, control stirring velocity at 160rpm, solution temperature controls at 35 DEG C, dripping massfraction is 45% solution of potassium carbonate 300ml, time for adding controls at 2h, add rear maintenance whipped state 5h, divide oil-yielding stratum, wash with potassium bromide solution successively, massfraction is 30% sodium sulfite solution washing, massfraction is 75% dimethylamine solution washing, calcium sulfate dewaters, 1.8kPa underpressure distillation, collect the cut of 140--145 DEG C, obtain methyl tosylate 38.31g, yield 76%.
Example 2:
Agitator is being installed, thermometer, in the reaction vessel of dropping funnel, add tolysulfonyl bromine (2) 0.271mol, 2, 2, 2-trifluoroethyl methyl ether 1.58mol, control stirring velocity at 170rpm, solution temperature controls at 37 DEG C, dripping massfraction is 47% solution of potassium carbonate 300ml, time for adding controls at 2.5h, add rear maintenance whipped state 5h, divide oil-yielding stratum, wash with sodium chloride solution successively, massfraction is 33% sodium sulfite solution washing, massfraction is 78% dimethylamine solution washing, activated alumina dewaters, 1.85kPa underpressure distillation, collect the cut of 140--145 DEG C, obtain methyl tosylate 39.82g, yield 79%.
Example 3:
Agitator is being installed, thermometer, in the reaction vessel of dropping funnel, add tolysulfonyl bromine (2) 0.271mol, 2, 2, 2-trifluoroethyl methyl ether 1.59mol, control stirring velocity at 190rpm, solution temperature controls at 40 DEG C, dripping massfraction is 50% solution of potassium carbonate 300ml, time for adding controls at 3h, add rear maintenance whipped state 6h, divide oil-yielding stratum, wash with potassium bromide solution successively, massfraction is 35% sodium sulfite solution washing, massfraction is 80% dimethylamine solution washing, calcium sulfate dewaters, 1.9kPa underpressure distillation, collect the cut of 140--145 DEG C, obtain methyl tosylate 42.34g, yield 84%.
Claims (5)
1. a synthetic method for selective methylation reagent methyl tosylate, is characterized in that, comprises the steps:
I () is being provided with agitator, thermometer, in the reaction vessel of dropping funnel, add tolysulfonyl bromine (2) 0.271mol, 2, 2, 2-trifluoroethyl methyl ether 1.57-1.59mol, control stirring velocity at 160-190rpm, solution temperature controls at 35--40 DEG C, drip solution of potassium carbonate 300ml, time for adding controls at 2-3h, add rear maintenance whipped state 5-6h, divide oil-yielding stratum, use brine successively, sodium sulfite solution washs, dimethylamine solution washs, dewatering agent dewaters, underpressure distillation, collect the cut of 140--145 DEG C, obtain methyl tosylate (1),
Wherein, the massfraction of the solution of potassium carbonate described in step (i) is 45-50%, and the salts solution described in step (i) is any one in Potassium Bromide, sodium-chlor.
2. the synthetic method of a kind of selective methylation reagent methyl tosylate according to claim 1, it is characterized in that, the massfraction of the sodium sulfite solution described in step (i) is 30-35%.
3. the synthetic method of a kind of selective methylation reagent methyl tosylate according to claim 1, it is characterized in that, the massfraction of the dimethylamine solution described in step (i) is 75-80%.
4. the synthetic method of a kind of selective methylation reagent methyl tosylate according to claim 1, is characterized in that, the dewatering agent described in step (i) is any one in calcium sulfate, activated alumina.
5. the synthetic method of a kind of selective methylation reagent methyl tosylate according to claim 1, it is characterized in that, the underpressure distillation described in step (i), residing pressure is 1.8-1.9kPa.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510976362.9A CN105566172A (en) | 2015-12-22 | 2015-12-22 | Synthetic method of selective methylation reagent methyl p-toluenesulfonate |
| CN201610827791.4A CN106397277A (en) | 2015-12-22 | 2016-09-18 | Synthesis method of selective methylating agent methyl p-toluenesulfonate |
| AU2016102175A AU2016102175A4 (en) | 2015-12-22 | 2016-12-22 | Selective methylation reagent p-toluene sulfonic acid methyl ester synthesis method |
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| CN201510976362.9A CN105566172A (en) | 2015-12-22 | 2015-12-22 | Synthetic method of selective methylation reagent methyl p-toluenesulfonate |
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| CN105566172A true CN105566172A (en) | 2016-05-11 |
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| CN201510976362.9A Pending CN105566172A (en) | 2015-12-22 | 2015-12-22 | Synthetic method of selective methylation reagent methyl p-toluenesulfonate |
| CN201610827791.4A Pending CN106397277A (en) | 2015-12-22 | 2016-09-18 | Synthesis method of selective methylating agent methyl p-toluenesulfonate |
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| CN201610827791.4A Pending CN106397277A (en) | 2015-12-22 | 2016-09-18 | Synthesis method of selective methylating agent methyl p-toluenesulfonate |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109225312A (en) * | 2018-09-19 | 2019-01-18 | 南通沃兰化工有限公司 | A kind of synthetic method of methyl tosylate |
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2015
- 2015-12-22 CN CN201510976362.9A patent/CN105566172A/en active Pending
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2016
- 2016-09-18 CN CN201610827791.4A patent/CN106397277A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109225312A (en) * | 2018-09-19 | 2019-01-18 | 南通沃兰化工有限公司 | A kind of synthetic method of methyl tosylate |
| CN109225312B (en) * | 2018-09-19 | 2021-06-29 | 南通沃兰化工有限公司 | Synthesis method of methyl p-toluenesulfonate |
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| Publication number | Publication date |
|---|---|
| CN106397277A (en) | 2017-02-15 |
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Application publication date: 20160511 |