AU2016102175A4 - Selective methylation reagent p-toluene sulfonic acid methyl ester synthesis method - Google Patents
Selective methylation reagent p-toluene sulfonic acid methyl ester synthesis method Download PDFInfo
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- AU2016102175A4 AU2016102175A4 AU2016102175A AU2016102175A AU2016102175A4 AU 2016102175 A4 AU2016102175 A4 AU 2016102175A4 AU 2016102175 A AU2016102175 A AU 2016102175A AU 2016102175 A AU2016102175 A AU 2016102175A AU 2016102175 A4 AU2016102175 A4 AU 2016102175A4
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- sulfonic acid
- methyl ester
- acid methyl
- toluene sulfonic
- solution
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Abstract
Selective methylation reagent p-toluene sulfonic acid methyl ester synthesis method, comprising the following steps: equipped with a stirrer, a thermometer, a dropping funnel, a reaction vessel, was added 0.271mol p-toluenesulfonyl bromine (2), 1.57-1.59mol 2,2,2- trifluoroethyl methyl ether, controlling stirring speed at 160-190rpm, temperature controlled at 35--40'C, 300ml potassium carbonate solution was added, the dropping time was controlled in 2-3h, after addition maintaining the stirring for 5-6h, the oil was separated, washed with salt solution, sodium sulfite solution, dimethylamine solution successively, dehydrated with dehydrating agent, vacuum distillation, collecting the distillate of 140--145 C, got p-toluene sulfonic acid methyl ester.
Description
Selective methylation reagent p-toluene sulfonic acid methyl ester synthesis method
TECHNICAL FIELD
The present invention relates to selective methylation reagent p-toluene sulfonic acid methyl ester synthesis method.
BACKGROUND ART
As selective methylation reagents of organic synthesis, p-toluene sulfonic acid methyl ester is used for making dyes and organic synthesis, used as a raw material for preparing methylated, organic synthesis reagents and selective methylation catalyst, therefore, its synthesis method is of great economic significance for improving drug synthesis product quality, reducing the by-product content.
SUMMARY OF THE INVENTION
Object of the present invention is to provide selective methylation reagent p-toluene sulfonic acid methyl ester synthesis method, comprising the following steps: (i) equipped with a stirrer, a thermometer, a dropping funnel, a reaction vessel, was added 0.271 mol p-toluenesulfonyl bromine (2), 1.57-1.59mol 2,2,2- trifluoroethyl methyl ether, controlling stirring speed at 160-190rpm, temperature controlled at 35—40°C, 300ml potassium carbonate solution was added, the dropping time was controlled in 2-3h, after addition maintaining the stirring for 5-6h, the oil was separated, washed with salt solution, sodium sulfite solution, dimethylamine solution successively, dehydrated with dehydrating agent, vacuum distillation, collecting the distillate of 140—145 °C, got p-toluene sulfonic acid methyl ester (1); wherein, the potassium carbonate solution in step (i) has a mass fraction of 45-50%, the salt solution in step (i) is any one of potassium bromide, sodium chloride, the sodium sulfite solution in step (i) has a mass fraction of is 30-35%, the dimethylamine solution in step (i) has a mass fraction of 75-80%, the dehydrating agent in step (i) is any one of calcium sulfate, activated alumina, the vacuum distillation in step (i), has a pressure of 1.8-1.9kPa.
Throughout the reaction can be summarized as the following reaction formula:
{2)
Advantage of the present invention is that: reducing the reaction intermediate links, decreasing the reaction temperature and reaction time, improving the reaction yield.
DETAILED DESCRIPTION OF PREFERRED EMBODIMENTS OF THE INVENTION
Embodiment 1
Equipped with a stirrer, a thermometer, a dropping funnel, a reaction vessel, was added 0.27lmol p-toluenesulfonyl bromine (2), 1.57mol 2,2,2- trifluoroethyl methyl ether, controlling stirring speed at 160rpm, temperature controlled at 35 °C, 300ml potassium carbonate solution with a mass fraction of 45%was added, the dropping time was controlled in 2h, after addition maintaining the stirring for 5h, the oil was separated, washed with potassium bromide solution, sodium sulfite solution with a mass fraction of is 30%, dimethylamine solution with a mass fraction of 75% successively, dehydrated with calcium sulfate, vacuum distillation at 1.8kPa, collecting the distillate of 140—145 °C, got p-toluene sulfonic acid methyl ester (1) 38.3 lg,yield 76%.
Embodiment 2
Equipped with a stirrer, a thermometer, a dropping funnel, a reaction vessel, was added 0.271mol p-toluenesulfonyl bromine (2), 1.58mol 2.2.2- trifluoroethyl methyl ether, controlling stirring speed at 170rpm, temperature controlled at 37 °C, 300ml potassium carbonate solution with a mass fraction of 47%was added, the dropping time was controlled in 2.5h, after addition maintaining the stirring for 5h, the oil was separated, washed with sodium chloride solution, sodium sulfite solution with a mass fraction of is 33%, dimethylamine solution with a mass fraction of 78% successively, dehydrated with activated alumina, vacuum distillation at 1.85kPa, collecting the distillate of 140—145 °C, got p-toluene sulfonic acid methyl ester (1) 39.82g,yield 79%.
Embodiment 3
Equipped with a stirrer, a thermometer, a dropping funnel, a reaction vessel, was added 0.27lmol p-toluenesulfonyl bromine (2), 1.59mol 2.2.2- trifluoroethyl methyl ether, controlling stirring speed at 190rpm, temperature controlled at 40 °C, 300ml potassium carbonate solution with a mass fraction of 50%was added, the dropping time was controlled in 3h, after addition maintaining the stirring for 6h, the oil was separated, washed with potassium bromide solution, sodium sulfite solution with a mass fraction of is 35%, dimethylamine solution with a mass fraction of 80% successively, dehydrated with calcium sulfate, vacuum distillation at 1.9kPa, collecting the distillate of 140—145 °C, got p-toluene sulfonic acid methyl ester (1) 42.34g,yield 84%.
While a number of preferred embodiments have been described, it will be appreciated by persons skilled in the art that numerous variations and/or modifications may be made to the invention without departing from the spirit or scope of the invention as broadly described. The present embodiments are, therefore, to be considered in all respects as illustrative and not restrictive.
Claims (4)
1. Selective methylation reagent p-toluene sulfonic acid methyl ester synthesis method, comprising the following steps: (i) equipped with a stirrer, a thermometer, a dropping funnel, a reaction vessel, was added 0.271mol p-toluenesulfonyl bromine (2), 1.57-1.59mol 2,2,2- trifluoroethyl methyl ether, controlling stirring speed at 160-190rpm, temperature controlled at 35—40 °C , 300ml potassium carbonate solution was added, the dropping time was controlled in 2-3h, after addition maintaining the stirring for 5-6h, the oil was separated, washed with salt solution, sodium sulfite solution, dimethylamine solution successively, dehydrated with dehydrating agent, vacuum distillation, collecting the distillate of 140—145 °C, got p-toluene sulfonic acid methyl ester (1); wherein, the potassium carbonate solution in step (i) has a mass fraction of 45-50%, the salt solution in step (i) is any one of potassium bromide, sodium chloride, the sodium sulfite solution in step (i) has a mass fraction of is 30-35%.
2. Selective methylation reagent p-toluene sulfonic acid methyl ester synthesis method according to claim 1 wherein the dimethylamine solution in step (i) has a mass fraction of 75-80%.
3. Selective methylation reagent p-toluene sulfonic acid methyl ester synthesis method according to claim 1 wherein the dehydrating agent in step (i) is any one of calcium sulfate, activated alumina.
4. Selective methylation reagent p-toluene sulfonic acid methyl ester synthesis method according to claim 1 wherein the vacuum distillation in step (i), has a pressure of 1.8-1.9kPa.
Applications Claiming Priority (4)
| 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 |
| CN2015109763629 | 2015-12-22 | ||
| CN201610827791.4A CN106397277A (en) | 2015-12-22 | 2016-09-18 | Synthesis method of selective methylating agent methyl p-toluenesulfonate |
| CN2016108277914 | 2016-09-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2016102175A4 true AU2016102175A4 (en) | 2017-02-16 |
Family
ID=57996345
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2016102175A Ceased AU2016102175A4 (en) | 2015-12-22 | 2016-12-22 | Selective methylation reagent p-toluene sulfonic acid methyl ester synthesis method |
Country Status (1)
| Country | Link |
|---|---|
| AU (1) | AU2016102175A4 (en) |
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2016
- 2016-12-22 AU AU2016102175A patent/AU2016102175A4/en not_active Ceased
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| MK22 | Patent ceased section 143a(d), or expired - non payment of renewal fee or expiry |