CN102757337A - Method for preparing hydroxyphenylacetic acid - Google Patents
Method for preparing hydroxyphenylacetic acid Download PDFInfo
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- CN102757337A CN102757337A CN2012102686149A CN201210268614A CN102757337A CN 102757337 A CN102757337 A CN 102757337A CN 2012102686149 A CN2012102686149 A CN 2012102686149A CN 201210268614 A CN201210268614 A CN 201210268614A CN 102757337 A CN102757337 A CN 102757337A
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- sodium hydroxide
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Abstract
The invention discloses a method for preparing hydroxyphenylacetic acid by taking chlorobenzyl chloride as raw material in a one-pot manner. The method comprises the following steps: mixing chlorobenzyl chloride and triethylamine, controlling the temperature to be 80 DEG C-100 DEG C, dropwise adding sodium cyanide water solutionk after adding, keeping the temperature at 80 DEG C-100 DEG C, stirring and reacting; after the reaction, cooling reaction liquid, adding excessive sodium hydroxide, raising the temperature to be 100 DEG C-110 DEG C, keeping the temperature, stirring and reacting; after the reaction, cooling reaction liquid, and transferring the reaction liquid into a high-pressure kettle, supplementing sodium hydroxide according to the sodium hydroxide which is not reacted completely in the reaction liquid, adding a catalyst, namely copper sulfate, raising the temperature to be 180 DEG C-200 DEG C, keeping the temperature, stirring and reacting; and after the reaction, cooling the reaction liquid, adding acid for acidizing until the pH value is 1, separating solid from liquid, washing the solid with water, and drying to obtain hydroxyphenylacetic acid. According to the method, products in each step of reaction do not need to be separated and purified, the operation is simple and convenient, the time is saved, the consumption of the raw materials (alkali and acid) and generation of byproduct salt are reduced, and the product yield is high.
Description
Technical field
The invention belongs to organic chemistry filed, relate to the preparation method of one type of organic cpds.
Background technology
O-hydroxy phenylacetic acid is the important intermediate of synthetic medicine (for example sterilant ICIA 5504).Its preparation method be with NSC 4613 and sodium hydroxide under copper 8-quinolinolate (II) catalysis, react under 170 ℃ of the temperature, pressure 650 ~ 700kPa condition, make with acidifying again.And the raw material NSC 4613 can make adjacent chlorobenzene acetonitrile through adjacent chlorobenzyl chloride and sodium cyanide reaction, and the latter is hydrolyzed and makes.Promptly with adjacent chlorobenzyl chloride be starting raw material prepare o-hydroxy phenylacetic acid need divide three the step carry out; Per step reaction all need be carried out separation and purification treatment to resultant of reaction after finishing; Complex operation, consuming time not only; Starting material (alkali and acid) consume with by-product salt growing amount big, and cause product loss, yield lower.
Summary of the invention
In view of this; The object of the present invention is to provide a kind of is the method that starting raw material, one pot of change prepare o-hydroxy phenylacetic acid with adjacent chlorobenzyl chloride; Need not carry out separation and purification treatment to the resultant of per step reaction; Easy and simple to handle, save time, reduce the consumption of starting material (alkali and acid) and the growing amount of by-product salt, improve product yield.
For achieving the above object, the present invention provides following technical scheme:
The preparation method of o-hydroxy phenylacetic acid may further comprise the steps: adjacent chlorobenzyl chloride and triethylamine are mixed, and temperature control 80-100 ℃ drips sodium cyanide solution; The mol ratio of said adjacent chlorobenzyl chloride, triethylamine and sodium cyanide is 10:1:10-11, after dropwising, and 80-100 ℃ of insulated and stirred reaction; The content of adjacent chlorobenzyl chloride is lower than 1% o'clock stopped reaction to the reaction solution, with the reaction solution cooling, adds and is equivalent to adjacent chlorobenzyl chloride molar weight 1.2-2.0 sodium hydroxide doubly; Be warming up to 105-110 ℃ of insulated and stirred reaction again, stopped reaction when no ammonia is emitted to system cools off reaction solution; Be transferred in the autoclave, the 4-5 that the integral molar quantity of adding sodium hydroxide to sodium hydroxide according to the amount of the intact sodium hydroxide of unreacted in the reaction solution is equivalent to adjacent chlorobenzyl chloride molar weight doubly adds the copper sulfate that is equivalent to adjacent chlorobenzyl chloride molar weight 3%-5% again; Be warming up to the reaction of 180-200 ℃ of insulated and stirred, to NSC 4613 content less than 0.5% o'clock stopped reaction, reaction solution is cooled off; Adding acid, to be acidified to pH be 1; Solid-liquid separation, solids wash, drying promptly obtain o-hydroxy phenylacetic acid.
Preferably, the preparation method of said o-hydroxy phenylacetic acid may further comprise the steps: adjacent chlorobenzyl chloride and triethylamine are mixed, and temperature control 95-100 ℃ drips sodium cyanide solution, and the mol ratio of said adjacent chlorobenzyl chloride, triethylamine and sodium cyanide is 10:1:11; After dropwising, 95-100 ℃ of insulated and stirred reacted 1.5 hours, and reaction solution is cooled to room temperature; Add the sodium hydroxide be equivalent to 2 times of adjacent chlorobenzyl chloride molar weights, be warming up to 110 ℃ of insulated and stirred reactions 2.5 hours again, during the ammonia that generates of water absorption reaction; Reaction is cooled to room temperature with reaction solution after accomplishing, and is transferred in the autoclave; The integral molar quantity of adding sodium hydroxide to sodium hydroxide according to the amount of the intact sodium hydroxide of unreacted in the reaction solution is equivalent to 4 times of adjacent chlorobenzyl chloride molar weight, adds the cupric sulfate pentahydrate that is equivalent to adjacent chlorobenzyl chloride molar weight 5% again, is warming up to 200 ℃ of insulated and stirred reactions 4 hours; Reaction solution is cooled to room temperature, and the enriching hcl acidifying is 1 to pH, solid-liquid separation; Solid is used water washing, and drying promptly obtains o-hydroxy phenylacetic acid.
Preferably, the preparation method of said o-hydroxy phenylacetic acid may further comprise the steps: adjacent chlorobenzyl chloride and triethylamine are mixed, and temperature control 80-85 ℃ drips sodium cyanide solution, and the mol ratio of said adjacent chlorobenzyl chloride, triethylamine and sodium cyanide is 10:1:10; After dropwising, 80-85 ℃ of insulated and stirred reacted 2 hours, and reaction solution is cooled to room temperature; Add the sodium hydroxide be equivalent to 2 times of adjacent chlorobenzyl chloride molar weights, be warming up to 110 ℃ of insulated and stirred reactions 2.5 hours again, during the ammonia that generates of water absorption reaction; Reaction is cooled to room temperature with reaction solution after accomplishing, and is transferred in the autoclave; The integral molar quantity of adding sodium hydroxide to sodium hydroxide according to the amount of the intact sodium hydroxide of unreacted in the reaction solution is equivalent to 4 times of adjacent chlorobenzyl chloride molar weight, adds the cupric sulfate pentahydrate that is equivalent to adjacent chlorobenzyl chloride molar weight 3% again, is warming up to 200 ℃ of insulated and stirred reactions 4 hours; Reaction solution is cooled to room temperature, and the enriching hcl acidifying is 1 to pH, solid-liquid separation; Solid is used water washing, and drying promptly obtains o-hydroxy phenylacetic acid.
Preferably, the preparation method of said o-hydroxy phenylacetic acid may further comprise the steps: adjacent chlorobenzyl chloride and triethylamine are mixed, and temperature control 95-100 ℃ drips sodium cyanide solution, and the mol ratio of said adjacent chlorobenzyl chloride, triethylamine and sodium cyanide is 10:1:11; After dropwising, 95-100 ℃ of insulated and stirred reacted 1.5 hours, and reaction solution is cooled to room temperature; Add the sodium hydroxide be equivalent to 2 times of adjacent chlorobenzyl chloride molar weights, be warming up to 110 ℃ of insulated and stirred reactions 2.5 hours again, during the ammonia that generates of water absorption reaction; Reaction is cooled to room temperature with reaction solution after accomplishing, and is transferred in the autoclave; The integral molar quantity of adding sodium hydroxide to sodium hydroxide according to the amount of the intact sodium hydroxide of unreacted in the reaction solution is equivalent to 4 times of adjacent chlorobenzyl chloride molar weight, adds the cupric sulfate pentahydrate that is equivalent to adjacent chlorobenzyl chloride molar weight 5% again, is warming up to 180 ℃ of insulated and stirred reactions 6 hours; Reaction solution is cooled to room temperature, and the enriching hcl acidifying is 1 to pH, solid-liquid separation; Solid is used water washing, and drying promptly obtains o-hydroxy phenylacetic acid.
Best, the preparation method of said o-hydroxy phenylacetic acid may further comprise the steps: adjacent chlorobenzyl chloride and triethylamine are mixed, and temperature control 95-100 ℃ drips sodium cyanide solution, and the mol ratio of said adjacent chlorobenzyl chloride, triethylamine and sodium cyanide is 10:1:11; After dropwising, 95-100 ℃ of insulated and stirred reacted 1.5 hours, and reaction solution is cooled to room temperature; Add the sodium hydroxide be equivalent to 1.5 times of adjacent chlorobenzyl chloride molar weights, be warming up to 105 ℃ of insulated and stirred reactions 3.5 hours again, during the ammonia that generates of water absorption reaction; Reaction is cooled to room temperature with reaction solution after accomplishing, and is transferred in the autoclave; The integral molar quantity of adding sodium hydroxide to sodium hydroxide according to the amount of the intact sodium hydroxide of unreacted in the reaction solution is equivalent to 5 times of adjacent chlorobenzyl chloride molar weight, adds the cupric sulfate pentahydrate that is equivalent to adjacent chlorobenzyl chloride molar weight 5% again, is warming up to 195 ℃ of insulated and stirred reactions 4 hours; Reaction solution is cooled to room temperature, and the enriching hcl acidifying is 1 to pH, solid-liquid separation; Solid is used water washing, and drying promptly obtains o-hydroxy phenylacetic acid.
Beneficial effect of the present invention is: the invention provides a kind of is the method that starting raw material, one pot of change prepare o-hydroxy phenylacetic acid with adjacent chlorobenzyl chloride; Need not carry out separation and purification treatment to the resultant of per step reaction; Easy and simple to handle, save time; Reduced the consumption of starting material (alkali and acid) and the growing amount of by-product salt, product yield is high.
Embodiment
In order to make the object of the invention, technical scheme and advantage clearer, will carry out detailed description to the preferred embodiments of the present invention below.Should be appreciated that preferred embodiment has been merely explanation the present invention, rather than in order to limit protection scope of the present invention.
Embodiment 1
Be equipped with in the four-hole bottle of reflux exchanger, TM, whisking appliance and constant voltage separating funnel one, (content 98.5% 0.2mol) with triethylamine 2.0g (0.02mol), stirs and is warming up to 95 ℃, under temperature 95-100 ℃ condition, drips sodium cyanide solution 40.0g (content 27% to add adjacent chlorobenzyl chloride 32.7g; 0.22mol), finished 95-100 ℃ of stirring reaction of insulation 1.5 hours, sampling analysis, the content of adjacent chlorobenzyl chloride is 0.32% in the reaction solution, reaction is accomplished; Reaction solution is cooled to room temperature, and (content 99% 0.4mol), is warming up to 110 ℃ of insulated and stirred reactions to add sodium hydroxide 16.2g; The ammonia that the water absorption reaction generates, no ammonia generation in the system after 2.5 hours, stopped reaction is cooled to room temperature with reaction solution; Sampling analysis, reaction solution include sodium hydroxide 7.6g (0.19mol), and reaction solution is transferred in the autoclave, add sodium hydroxide 24.6g (content 99%; 0.61mol), (content 98% 0.01mol), is warming up to 200 ℃ of insulated and stirred reactions 4 hours to add cupric sulfate pentahydrate 2.55g again; Sampling analysis, the content of NSC 4613 is 0.08% in the reaction solution, reaction is accomplished, and reaction solution is cooled to room temperature; The enriching hcl acidifying filters to pH=1, and solid is dried with 30ml water washing 3 times; Get faint yellow solid 27.8g, analyze through HPLC, o-hydroxy phenylacetic acid content is 98.1%, yield 89.7%.
Embodiment 2
Be equipped with in the four-hole bottle of reflux exchanger, TM, whisking appliance and constant voltage separating funnel one, (content 98.5% 0.2mol) with triethylamine 2.0g (0.02mol), stirs and is warming up to 80 ℃, under temperature 80-85 ℃ condition, drips sodium cyanide solution 36.4g (content 27% to add adjacent chlorobenzyl chloride 32.7g; 0.20mol), finished 80-85 ℃ of stirring reaction of insulation 2 hours, sampling analysis, the content of adjacent chlorobenzyl chloride is 0.45% in the reaction solution, reaction is accomplished; Reaction solution is cooled to room temperature, and (content 99% 0.4mol), is warming up to 110 ℃ of insulated and stirred reactions to add sodium hydroxide 16.2g; The ammonia that the water absorption reaction generates, no ammonia generation in the system after 2.5 hours, stopped reaction is cooled to room temperature with reaction solution; Sampling analysis, reaction solution include sodium hydroxide 7.2g (0.18mol), and reaction solution is transferred in the autoclave, add sodium hydroxide 25.0g (content 99%; 0.62mol), (content 98% 0.006mol), is warming up to 200 ℃ of insulated and stirred reactions 4 hours to add cupric sulfate pentahydrate 1.53g again; Sampling analysis, the content of NSC 4613 is 0.10% in the reaction solution, reaction is accomplished, and reaction solution is cooled to room temperature; The enriching hcl acidifying filters to pH=1, and solid is dried with 30ml water washing 3 times; Get faint yellow solid 27.4g, analyze through HPLC, o-hydroxy phenylacetic acid content is 98.3%, yield 88.5%.
Embodiment 3
Be equipped with in the four-hole bottle of reflux exchanger, TM, whisking appliance and constant voltage separating funnel one, (content 98.5% 0.2mol) with triethylamine 2.0g (0.02mol), stirs and is warming up to 95 ℃, under temperature 95-100 ℃ condition, drips sodium cyanide solution 40.0g (content 27% to add adjacent chlorobenzyl chloride 32.7g; 0.22mol), finished 95-100 ℃ of stirring reaction of insulation 1.5 hours, sampling analysis, the content of adjacent chlorobenzyl chloride is 0.36% in the reaction solution, reaction is accomplished; Reaction solution is cooled to room temperature, and (content 99% 0.4mol), is warming up to 110 ℃ of insulated and stirred reactions to add sodium hydroxide 16.2g; The ammonia that the water absorption reaction generates, no ammonia generation in the system after 2.5 hours, stopped reaction is cooled to room temperature with reaction solution; Sampling analysis, reaction solution include sodium hydroxide 8.0g (0.2mol), and reaction solution is transferred in the autoclave, add sodium hydroxide 24.2g (content 99%; 0.6mol), (content 98% 0.01mol), is warming up to 180 ℃ of insulated and stirred reactions 6 hours to add cupric sulfate pentahydrate 2.55g again; Sampling analysis, the content of NSC 4613 is 0.04% in the reaction solution, reaction is accomplished, and reaction solution is cooled to room temperature; The enriching hcl acidifying filters to pH=1, and solid is dried with 50ml water washing 2 times; Get faint yellow solid 28.0g, analyze through HPLC, o-hydroxy phenylacetic acid content is 97.6%, yield 90.1%.
Embodiment 4
Be equipped with in the four-hole bottle of reflux exchanger, TM, whisking appliance and constant voltage separating funnel one, (content 98.5% 0.2mol) with triethylamine 2.0g (0.02mol), stirs and is warming up to 95 ℃, under temperature 95-100 ℃ condition, drips sodium cyanide solution 40.0g (content 27% to add adjacent chlorobenzyl chloride 32.7g; 0.22mol), finished 95-100 ℃ of stirring reaction of insulation 1.5 hours, sampling analysis, the content of adjacent chlorobenzyl chloride is 0.28% in the reaction solution, reaction is accomplished; Reaction solution is cooled to room temperature, and (content 99% 0.3mol), is warming up to 105 ℃ of insulated and stirred reactions to add sodium hydroxide 12.2g; The ammonia that the water absorption reaction generates, no ammonia generation in the system after 3.5 hours, stopped reaction is cooled to room temperature with reaction solution; Sampling analysis, reaction solution include sodium hydroxide 3.6g (0.09mol), and reaction solution is transferred in the autoclave, add sodium hydrate solid 36.8g (content 99%; 0.91mol), (content 98% 0.01mol), is warming up to 195 ℃ of insulated and stirred reactions 4 hours to add cupric sulfate pentahydrate 2.55g again; Sampling analysis, the content of NSC 4613 is 0.01% in the reaction solution, reaction is accomplished, and reaction solution is cooled to room temperature; The enriching hcl acidifying filters to pH=1, and solid is dried with 50ml water washing 3 times; Get faint yellow solid 28.2g, analyze through HPLC, o-hydroxy phenylacetic acid content is 98.6%, yield 91.5%.
Claims (5)
1. the preparation method of o-hydroxy phenylacetic acid is characterized in that, may further comprise the steps: adjacent chlorobenzyl chloride and triethylamine are mixed; Temperature control 80-100 ℃ drips sodium cyanide solution, and the mol ratio of said adjacent chlorobenzyl chloride, triethylamine and sodium cyanide is 10:1:10-11, after dropwising; The reaction of 80-100 ℃ of insulated and stirred, the content of adjacent chlorobenzyl chloride is lower than 1% o'clock stopped reaction to the reaction solution, and reaction solution is cooled off; Add and be equivalent to adjacent chlorobenzyl chloride molar weight 1.2-2.0 sodium hydroxide doubly, be warming up to 105-110 ℃ of insulated and stirred reaction again, stopped reaction when no ammonia is emitted to system; With reaction solution cooling, be transferred in the autoclave, the 4-5 that the integral molar quantity of adding sodium hydroxide to sodium hydroxide according to the amount of the intact sodium hydroxide of unreacted in the reaction solution is equivalent to adjacent chlorobenzyl chloride molar weight is doubly; Add the copper sulfate be equivalent to adjacent chlorobenzyl chloride molar weight 3%-5% again, be warming up to 180-200 ℃ of insulated and stirred reaction, to NSC 4613 content less than 0.5% o'clock stopped reaction; With reaction solution cooling, adding acid, to be acidified to pH be 1, solid-liquid separation; Solids wash, drying promptly obtain o-hydroxy phenylacetic acid.
2. the preparation method of o-hydroxy phenylacetic acid according to claim 1 is characterized in that, may further comprise the steps: adjacent chlorobenzyl chloride and triethylamine are mixed; Temperature control 95-100 ℃ drips sodium cyanide solution, and the mol ratio of said adjacent chlorobenzyl chloride, triethylamine and sodium cyanide is 10:1:11, after dropwising; 95-100 ℃ of insulated and stirred reacted 1.5 hours, and reaction solution is cooled to room temperature, added the sodium hydroxide that is equivalent to 2 times of adjacent chlorobenzyl chloride molar weights; Be warming up to 110 ℃ of insulated and stirred reaction 2.5 hours again, during the ammonia that generates of water absorption reaction, after reaction is accomplished; Reaction solution is cooled to room temperature, is transferred in the autoclave, the integral molar quantity of adding sodium hydroxide to sodium hydroxide according to the amount of the intact sodium hydroxide of unreacted in the reaction solution is equivalent to 4 times of adjacent chlorobenzyl chloride molar weight; Add the cupric sulfate pentahydrate that is equivalent to adjacent chlorobenzyl chloride molar weight 5% again, be warming up to 200 ℃ of insulated and stirred reactions 4 hours, reaction solution is cooled to room temperature; The enriching hcl acidifying is 1 to pH, solid-liquid separation, and solid is used water washing; Drying promptly obtains o-hydroxy phenylacetic acid.
3. the preparation method of o-hydroxy phenylacetic acid according to claim 1 is characterized in that, may further comprise the steps: adjacent chlorobenzyl chloride and triethylamine are mixed; Temperature control 80-85 ℃ drips sodium cyanide solution, and the mol ratio of said adjacent chlorobenzyl chloride, triethylamine and sodium cyanide is 10:1:10, after dropwising; 80-85 ℃ of insulated and stirred reacted 2 hours, and reaction solution is cooled to room temperature, added the sodium hydroxide that is equivalent to 2 times of adjacent chlorobenzyl chloride molar weights; Be warming up to 110 ℃ of insulated and stirred reaction 2.5 hours again, during the ammonia that generates of water absorption reaction, after reaction is accomplished; Reaction solution is cooled to room temperature, is transferred in the autoclave, the integral molar quantity of adding sodium hydroxide to sodium hydroxide according to the amount of the intact sodium hydroxide of unreacted in the reaction solution is equivalent to 4 times of adjacent chlorobenzyl chloride molar weight; Add the cupric sulfate pentahydrate that is equivalent to adjacent chlorobenzyl chloride molar weight 3% again, be warming up to 200 ℃ of insulated and stirred reactions 4 hours, reaction solution is cooled to room temperature; The enriching hcl acidifying is 1 to pH, solid-liquid separation, and solid is used water washing; Drying promptly obtains o-hydroxy phenylacetic acid.
4. the preparation method of o-hydroxy phenylacetic acid according to claim 1 is characterized in that, may further comprise the steps: adjacent chlorobenzyl chloride and triethylamine are mixed; Temperature control 95-100 ℃ drips sodium cyanide solution, and the mol ratio of said adjacent chlorobenzyl chloride, triethylamine and sodium cyanide is 10:1:11, after dropwising; 95-100 ℃ of insulated and stirred reacted 1.5 hours, and reaction solution is cooled to room temperature, added the sodium hydroxide that is equivalent to 2 times of adjacent chlorobenzyl chloride molar weights; Be warming up to 110 ℃ of insulated and stirred reaction 2.5 hours again, during the ammonia that generates of water absorption reaction, after reaction is accomplished; Reaction solution is cooled to room temperature, is transferred in the autoclave, the integral molar quantity of adding sodium hydroxide to sodium hydroxide according to the amount of the intact sodium hydroxide of unreacted in the reaction solution is equivalent to 4 times of adjacent chlorobenzyl chloride molar weight; Add the cupric sulfate pentahydrate that is equivalent to adjacent chlorobenzyl chloride molar weight 5% again, be warming up to 180 ℃ of insulated and stirred reactions 6 hours, reaction solution is cooled to room temperature; The enriching hcl acidifying is 1 to pH, solid-liquid separation, and solid is used water washing; Drying promptly obtains o-hydroxy phenylacetic acid.
5. the preparation method of o-hydroxy phenylacetic acid according to claim 1 is characterized in that, may further comprise the steps: adjacent chlorobenzyl chloride and triethylamine are mixed; Temperature control 95-100 ℃ drips sodium cyanide solution, and the mol ratio of said adjacent chlorobenzyl chloride, triethylamine and sodium cyanide is 10:1:11, after dropwising; 95-100 ℃ of insulated and stirred reacted 1.5 hours, and reaction solution is cooled to room temperature, added the sodium hydroxide that is equivalent to 1.5 times of adjacent chlorobenzyl chloride molar weights; Be warming up to 105 ℃ of insulated and stirred reaction 3.5 hours again, during the ammonia that generates of water absorption reaction, after reaction is accomplished; Reaction solution is cooled to room temperature, is transferred in the autoclave, the integral molar quantity of adding sodium hydroxide to sodium hydroxide according to the amount of the intact sodium hydroxide of unreacted in the reaction solution is equivalent to 5 times of adjacent chlorobenzyl chloride molar weight; Add the cupric sulfate pentahydrate that is equivalent to adjacent chlorobenzyl chloride molar weight 5% again, be warming up to 195 ℃ of insulated and stirred reactions 4 hours, reaction solution is cooled to room temperature; The enriching hcl acidifying is 1 to pH, solid-liquid separation, and solid is used water washing; Drying promptly obtains o-hydroxy phenylacetic acid.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4412082A (en) * | 1981-03-13 | 1983-10-25 | Nissan Chemical Industries, Ltd. | Method for preparing 4-hydroxyphenylacetic acid |
| JPH0769972A (en) * | 1993-05-28 | 1995-03-14 | Soc Fr Hoechst | Preparation of hydroxyphenylacetic acid |
| CN102241651A (en) * | 2011-05-25 | 2011-11-16 | 江苏七洲绿色化工股份有限公司 | Preparation method of azoxystrobin intermediate |
| CN102586346A (en) * | 2012-02-24 | 2012-07-18 | 重庆邮电大学 | Bio-catalytic method for preparing o-hydroxyphenylacetic acid |
-
2012
- 2012-07-31 CN CN2012102686149A patent/CN102757337A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4412082A (en) * | 1981-03-13 | 1983-10-25 | Nissan Chemical Industries, Ltd. | Method for preparing 4-hydroxyphenylacetic acid |
| JPH0769972A (en) * | 1993-05-28 | 1995-03-14 | Soc Fr Hoechst | Preparation of hydroxyphenylacetic acid |
| CN102241651A (en) * | 2011-05-25 | 2011-11-16 | 江苏七洲绿色化工股份有限公司 | Preparation method of azoxystrobin intermediate |
| CN102586346A (en) * | 2012-02-24 | 2012-07-18 | 重庆邮电大学 | Bio-catalytic method for preparing o-hydroxyphenylacetic acid |
Non-Patent Citations (3)
| Title |
|---|
| 唐薰等: "邻氯氯苄的合成及其下游产品", 《氯碱工业》 * |
| 徐家业: "《有机合成化学及近代技术》", December 1997 * |
| 胡在君等: "相转移催化法合成邻氯苯乙腈", 《湖南大学学报(自然科学版)》 * |
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Application publication date: 20121031 |