CN101844978A - Synthesis method of 2-(2-chloroethoxy) acetic acid - Google Patents
Synthesis method of 2-(2-chloroethoxy) acetic acid Download PDFInfo
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- CN101844978A CN101844978A CN201010171810A CN201010171810A CN101844978A CN 101844978 A CN101844978 A CN 101844978A CN 201010171810 A CN201010171810 A CN 201010171810A CN 201010171810 A CN201010171810 A CN 201010171810A CN 101844978 A CN101844978 A CN 101844978A
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- chloroethoxy
- water
- nitric acid
- acetate
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- MHXJETVNZPUVEN-UHFFFAOYSA-N 2-(2-chloroethoxy)acetic acid Chemical compound OC(=O)COCCCl MHXJETVNZPUVEN-UHFFFAOYSA-N 0.000 title abstract description 5
- 238000001308 synthesis method Methods 0.000 title 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 19
- 238000006243 chemical reaction Methods 0.000 claims abstract description 18
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims abstract description 17
- 229910017604 nitric acid Inorganic materials 0.000 claims abstract description 17
- 238000000034 method Methods 0.000 claims abstract description 12
- HUTXVUPGARJNHM-UHFFFAOYSA-N 1-(2-chloroethoxy)ethanol Chemical compound CC(O)OCCCl HUTXVUPGARJNHM-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000002904 solvent Substances 0.000 claims abstract description 11
- 239000002994 raw material Substances 0.000 claims abstract description 8
- 239000002253 acid Substances 0.000 claims abstract description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 12
- 230000003647 oxidation Effects 0.000 claims description 9
- 238000007254 oxidation reaction Methods 0.000 claims description 9
- 238000010189 synthetic method Methods 0.000 claims description 7
- VIEULUYYQGUMIF-UHFFFAOYSA-N 2-chloroethyl ethaneperoxoate Chemical compound CC(=O)OOCCCl VIEULUYYQGUMIF-UHFFFAOYSA-N 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 4
- 125000006012 2-chloroethoxy group Chemical group 0.000 claims description 3
- 230000035484 reaction time Effects 0.000 claims description 2
- 230000001476 alcoholic effect Effects 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 239000003960 organic solvent Substances 0.000 abstract description 4
- 238000002360 preparation method Methods 0.000 abstract description 4
- 239000012847 fine chemical Substances 0.000 abstract description 2
- 230000001590 oxidative effect Effects 0.000 abstract description 2
- 230000002194 synthesizing effect Effects 0.000 abstract 2
- 150000007513 acids Chemical class 0.000 abstract 1
- 239000007800 oxidant agent Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 239000007789 gas Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Natural products CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000001035 drying Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- LECMBPWEOVZHKN-UHFFFAOYSA-N 2-(2-chloroethoxy)ethanol Chemical compound OCCOCCCl LECMBPWEOVZHKN-UHFFFAOYSA-N 0.000 description 3
- ZKLPARSLTMPFCP-UHFFFAOYSA-N Cetirizine Chemical compound C1CN(CCOCC(=O)O)CCN1C(C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 ZKLPARSLTMPFCP-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 229960001803 cetirizine Drugs 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 230000007613 environmental effect Effects 0.000 description 3
- 238000010025 steaming Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 230000001624 sedative effect Effects 0.000 description 2
- ZUZWLUYOVJTJAG-UHFFFAOYSA-N 2-(2-chloroethoxy)ethyl acetate Chemical compound CC(=O)OCCOCCCl ZUZWLUYOVJTJAG-UHFFFAOYSA-N 0.000 description 1
- UENGBOCGGKLVJJ-UHFFFAOYSA-N 2-chloro-1-(2,4-difluorophenyl)ethanone Chemical compound FC1=CC=C(C(=O)CCl)C(F)=C1 UENGBOCGGKLVJJ-UHFFFAOYSA-N 0.000 description 1
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 1
- JHUUPUMBZGWODW-UHFFFAOYSA-N 3,6-dihydro-1,2-dioxine Chemical compound C1OOCC=C1 JHUUPUMBZGWODW-UHFFFAOYSA-N 0.000 description 1
- JUTNOZNZLTVIEO-UHFFFAOYSA-N FCC(=O)O.ClC=C Chemical compound FCC(=O)O.ClC=C JUTNOZNZLTVIEO-UHFFFAOYSA-N 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- 206010039094 Rhinitis perennial Diseases 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000002052 anaphylactic effect Effects 0.000 description 1
- 239000000043 antiallergic agent Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 229910001430 chromium ion Inorganic materials 0.000 description 1
- LKLAOWLOTDVVGF-UHFFFAOYSA-N chromium(6+) oxygen(2-) sulfuric acid Chemical compound [O-2].[O-2].[O-2].[Cr+6].OS(O)(=O)=O LKLAOWLOTDVVGF-UHFFFAOYSA-N 0.000 description 1
- 208000030949 chronic idiopathic urticaria Diseases 0.000 description 1
- 206010072757 chronic spontaneous urticaria Diseases 0.000 description 1
- 208000024376 chronic urticaria Diseases 0.000 description 1
- 229940088529 claritin Drugs 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- ZFTFAPZRGNKQPU-UHFFFAOYSA-N dicarbonic acid Chemical compound OC(=O)OC(O)=O ZFTFAPZRGNKQPU-UHFFFAOYSA-N 0.000 description 1
- 229960004132 diethyl ether Drugs 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229960001340 histamine Drugs 0.000 description 1
- ZQDWXGKKHFNSQK-UHFFFAOYSA-N hydroxyzine Chemical compound C1CN(CCOCCO)CCN1C(C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 ZQDWXGKKHFNSQK-UHFFFAOYSA-N 0.000 description 1
- 229960000930 hydroxyzine Drugs 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- JCCNYMKQOSZNPW-UHFFFAOYSA-N loratadine Chemical compound C1CN(C(=O)OCC)CCC1=C1C2=NC=CC=C2CCC2=CC(Cl)=CC=C21 JCCNYMKQOSZNPW-UHFFFAOYSA-N 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 230000002906 microbiologic effect Effects 0.000 description 1
- 210000002200 mouth mucosa Anatomy 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 208000022719 perennial allergic rhinitis Diseases 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000002464 receptor antagonist Substances 0.000 description 1
- 229940044551 receptor antagonist Drugs 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
一种2-(2-氯乙氧基)乙酸的合成方法，属于精细化工产品的制备及应用的技术领域，具体来说属于一种2-(2-氯乙氧基)乙酸的合成方法。本发明以2-氯乙氧基乙醇为起始原料，以水作溶剂用硝酸直接氧化得到产物，其反应过程如图。本发明采用水做溶剂，硝酸作为氧化剂，将2-氯乙氧基乙醇高效的氧化成相应的酸，该方法操作简便，原料廉价易得，对设备要求简单，以及后处理简单等优点，并且有机溶剂的使用近乎零成本，符合绿色环保的工业化生产要求，因此本发明具有很广阔的应用前景。
A method for synthesizing 2-(2-chloroethoxy)acetic acid belongs to the technical field of preparation and application of fine chemical products, specifically a method for synthesizing 2-(2-chloroethoxy)acetic acid. In the present invention, 2-chloroethoxyethanol is used as a starting material, water is used as a solvent and nitric acid is directly oxidized to obtain a product, and the reaction process is as shown in the figure. The present invention uses water as a solvent and nitric acid as an oxidant to efficiently oxidize 2-chloroethoxyethanol into corresponding acids. The method has the advantages of simple operation, cheap and easy-to-obtain raw materials, simple requirements for equipment, and simple post-treatment, etc., and The cost of using the organic solvent is almost zero, which meets the requirements of green and environment-friendly industrialized production, so the present invention has very broad application prospects.
Description
Technical field
The invention belongs to the technical field of the preparation and the application of fine chemical product, belong to the synthetic method of a kind of 2-(2-chloroethoxy) acetate specifically.
Background technology
2-chloroethoxy acetate has another name called: 2-(2-chloroethoxy) acetate, chloroethene fluoroacetic acid and 2-chlorine 2 '-the carboxyl ether; English name: 2-Chloroethoxyacetic acid, chloroethoxyacetic acid and 2-Chloro-2 '-carboxyl diethylether, be a kind of soluble in water, the colourless transparent liquid of organic solvents such as alcohol, ether, density: 1.326g/ml, boiling point: 130-132 ℃ (5mmHg).Molecular formula: C
4H
7O
3Cl, molecular weight: 138.5, be a kind of synthetic non-sedating histamine H
1The important intermediate of receptor antagonist Claritin cetrizine hcl, cetirizine are one of best-selling Claritins in the world at present, are a kind of anti-allergic drugs, and long lasting selectivity and strong H are arranged
1Receptor active, and do not have calm side effect.The anaphylactic disease that is used for respiratory system, skin and eye comprises chronic idiopathic urticaria, perennial allergic rhinitis, spring fever, slight sedative effect or oral mucosa drying etc.Compound of the present invention also is important solvent of a class and chemical reaction reagent, such as the necessary raw material that is synthetic medicine and pesticide intermediate 2-(2-chloroethoxy) methyl acetate and 2-(2-chloroethoxy) ethyl acetate etc.
Because of the vital role of this compounds, so 2-(2-chloroethoxy) acetate has very high practical value at medical field and chemical field.Usually the method for synthetic this compound is to adopt ethylene chlorhydrin and Mono Chloro Acetic Acid condensation, and by product is many and be difficult to remove.There is report to make 2-oxo-1 by the glycol ether catalytic dehydrogenation, behind the 4-dioxane, generate 2-(2-chloroethoxy) acetic ester with sulfur oxychloride and the reaction of corresponding low-carbon alcohol, acid hydrolysis obtains 2-(2-chloroethoxy) acetate (chemical research and application, 2001 again, 13 (5), 534-536), glycol ether is the by product of industrial preparation ethylene glycol, and it is limited to originate, preparation process complexity, and yield not high (about 48%); There is report 2-(2-chloroethoxy) oxidation of ethanol to be prepared 2-(2-chloroethoxy) acetate (KIENER ANDREASDR with microbial method, GLOCKLER RAINER.Microbiological prepn.of glycolic acid ether (s): CH, 686003[P], 1995-11-30), yield 87%, but the processing requirement height, the purifying products difficulty; Report Qiong Shi reagent (chromium trioxide-sulfuric acid) is arranged, or make oxygenant with oxygen and platinum dioxide and directly hydroxyzine is oxidized to cetirizine (TA0Y, KARIMIAN K TAM T.Methodsfor the manufacture of cetirizine:WO, 02425[P], 1998-01-22), reaction process is simple, but easily introduces chromium ion and nitrogen oxidized byproduct in the product, has a strong impact on quality product; Simultaneously also have pertinent literature to obtain corresponding acid (Hunan Normal University's journal, 2008,31 (2) 84-86) with the method direct oxidation alcohol of nitric acid direct oxidation, but use propyl carbinol as extraction agent in document aftertreatment, cost is higher.
Summary of the invention
The object of the present invention is to provide a kind of not only efficient but also economic method that meets Synthetic 2-(2-chloroethoxy) acetate that green synthetic is suitable for producing in enormous quantities.
The synthetic method of 2-of the present invention (2-chloroethoxy) acetate is a starting raw material with 2-chloroethoxy ethanol, obtains product with water as solvent with the nitric acid direct oxidation, its reaction process such as Fig. 1.
Nitric acid is as oxygenant, and its consumption is 1-5 a times of 2-chloroethoxy ethanol amount of substance.
Water is as solvent, and the consumption of water is 2-4 a times of 2-chloroethoxy ethanol quality.
Temperature of reaction is at 10 ℃-100 ℃.
The mass percentage concentration of used concentrated nitric acid is 10%-65%
Reaction times is 18-24 hour.
The present invention adopts water to make solvent, nitric acid is as oxygenant, 2-chloroethoxy ethanol is oxidized to corresponding acid efficiently, this method is easy and simple to handle, and raw material is cheap and easy to get, and is simple to equipment requirements, and advantage such as aftertreatment is simple, and the use near-zero cost of organic solvent meet the suitability for industrialized production requirement of environmental protection, so the present invention has very wide application prospect.
The present invention's after drying that directly dewaters need not to use extraction agent.Endanger little, good economy performance, environmental friendliness.
The present invention has these points advantage: 1. the present invention adopts 2-chloroethoxy ethanol as starting raw material, and raw material is cheap and easy to get.2. the present invention adopts nitric acid as oxygenant, does not almost have directly to use nitric acid that the oxidation of ethanol of 2-chloroethoxy is become corresponding acid in document in the past, and relative other oxygenant cheapnesss of nitric acid.3. the present invention adopts the water as solvent that cost is almost equal to zero, the organic solvent cheapness that adopts in the relative additive method, environmental protection.4. the present invention is the oxidizing reaction of carrying out at ambient temperature, and some reacting by heating have further reduced production cost relatively.5. aftertreatment of the present invention is simple, and refuse is environmentally friendly, makees solvent with water, the productive rate that room temperature just can reach more than 90% in 20 hours, so the present invention has very high superiority in industrial production.
Description of drawings
Fig. 1 is to be starting raw material with 2-chloroethoxy ethanol, obtains the reaction process figure of product with the nitric acid direct oxidation with water as solvent.
Embodiment:
The method of Synthetic 2 of the present invention-(2-chloroethoxy) acetate is as follows:
Embodiment 1
The 150ml there-necked flask that backflow and gas absorbing device are housed is chilled to 0-5 ℃, adds 2-(2-chloroethoxy) ethanol 12.45g (0.1mol), under this temperature, slowly add with the water-reducible concentrated nitric acid 9.7ml of 24.9mL (0.1mol).Finish, water-bath 30-35 ℃ of following stirring reaction 20h, reheat to 80～90 ℃ produce a large amount of reddish-brown NO
2Gas, stirring reaction is to no longer producing gas.Be cooled to room temperature, reaction solution is poured in the frozen water of 100ml, stir 1-2h, behind the most of water of pressure reducing and steaming, anhydrous sodium sulfate drying, filter, carry out underpressure distillation then and collect 130～132 ℃, the cut of 0.67kPa obtains colourless liquid 13.2g, be 2-(2-chloroethoxy) acetate, yield: 95%.
1HNMR(400MHz，CDCl
3)：δ(ppm)4.24(s，2H)，3.86(t，2H，)，3.69(t，2H，).
Embodiment 2
The 150mL there-necked flask that backflow and gas absorbing device are housed is chilled to 0-5 ℃, adds 2-(2-chloroethoxy) ethanol 12.45g (0.1mol), under this temperature, slowly add with the water-reducible concentrated nitric acid 24.3ml of 24.9mL (0.25mol).Finish, water-bath 30-40 ℃ of following stirring reaction 20h, reheat to 80～90 ℃ produce a large amount of reddish-brown NO
2Gas, stirring reaction is to no longer producing gas.Be cooled to room temperature, reaction solution is poured in the frozen water of 100ml, stir 1-2h, behind the most of water of pressure reducing and steaming, anhydrous sodium sulfate drying, filter, carry out underpressure distillation then and collect 130～132 ℃, the cut of 0.67kPa obtains colourless liquid 13.2g, be 2-(2-chloroethoxy) acetate, yield: 95%.
1HNMR(400MHz，CDCl
3)：δ(ppm)4.24(s，2H)，3.86(t，2H，)，3.69(t，2H，).
Embodiment 3
The 150mL there-necked flask that backflow and gas absorbing device are housed is chilled to 0-5 ℃, adds 2-(2-chloroethoxy) ethanol 12.45g (0.1mol), under this temperature, slowly add with the water-reducible concentrated nitric acid 48.5ml of 49.8mL (0.5mol).Finish, water-bath 50-60 ℃ of following stirring reaction 20h, reheat to 80～90 ℃ produce a large amount of reddish-brown NO
2Gas, stirring reaction is to no longer producing gas.Be cooled to room temperature, reaction solution is poured in the frozen water of 100ml, stir 1-2h, behind the most of water of pressure reducing and steaming, anhydrous sodium sulfate drying, filter, carry out underpressure distillation then and collect 130～132 ℃, the cut of 0.67kPa obtains colourless liquid 13.2g, be 2-(2-chloroethoxy) acetate, yield: 95%.
1HNMR(400MHz，CDCl
3)：δ(ppm)4.24(s，2H)，3.86(t，2H，)，3.69(t，2H，)。
Claims (6)
1. the synthetic method of a 2-(2-chloroethoxy) acetate is characterized in that, is starting raw material with 2-chloroethoxy ethanol, obtains product with water as solvent with the nitric acid direct oxidation, its reaction process such as Fig. 1.
2. the synthetic method of 2-as claimed in claim 1 (2-chloroethoxy) acetate,, it is characterized in that nitric acid is as oxygenant, its consumption is 1-5 a times of 2-chloroethoxy ethanol amount of substance.
3. the synthetic method of 2-as claimed in claim 1 (2-chloroethoxy) acetate is characterized in that, water is as solvent, and the consumption of water is 2-4 a times of 2-chloroethoxy ethanol quality.
4. the synthetic method of 2-as claimed in claim 1 (2-chloroethoxy) acetate is characterized in that, temperature of reaction is at 10 ℃-100 ℃.
5. 2-chloroethoxy alcoholic acid method for oxidation as claimed in claim 1, the mass percentage concentration of used concentrated nitric acid is 10%-65%.
6. 2-chloroethoxy alcoholic acid method for oxidation as claimed in claim 1, the reaction times is 18-24 hour.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102503809A (en) * | 2011-11-01 | 2012-06-20 | 台州市汇恩化工有限公司 | Method for synthesizing cefodizime acid side chain intermediate |
| CN103508879A (en) * | 2013-09-22 | 2014-01-15 | 江苏德峰药业有限公司 | Synthesis method of halogenated alkoxyl acetic acid |
| CN114380763A (en) * | 2020-10-16 | 2022-04-22 | 上海茂晟康慧科技有限公司 | Synthesis method of Ribosban intermediate 4- (4-aminophenyl) morpholine-3-one |
-
2010
- 2010-05-14 CN CN201010171810A patent/CN101844978A/en active Pending
Non-Patent Citations (1)
| Title |
|---|
| 杨小红等: "2-(2-氯乙氧基)乙酸的合成", 《湖南师范大学自然科学学报》 * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102503809A (en) * | 2011-11-01 | 2012-06-20 | 台州市汇恩化工有限公司 | Method for synthesizing cefodizime acid side chain intermediate |
| CN102503809B (en) * | 2011-11-01 | 2015-01-21 | 浙江工业大学 | Method for synthesizing cefodizime acid side chain intermediate |
| CN103508879A (en) * | 2013-09-22 | 2014-01-15 | 江苏德峰药业有限公司 | Synthesis method of halogenated alkoxyl acetic acid |
| CN103508879B (en) * | 2013-09-22 | 2015-10-21 | 江苏德峰药业有限公司 | A kind of synthetic method of haloalkoxy guanidine-acetic acid |
| CN114380763A (en) * | 2020-10-16 | 2022-04-22 | 上海茂晟康慧科技有限公司 | Synthesis method of Ribosban intermediate 4- (4-aminophenyl) morpholine-3-one |
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Application publication date: 20100929 |