CN115304481A - Preparation method of dimethyl dialkyl malonate - Google Patents
Preparation method of dimethyl dialkyl malonate Download PDFInfo
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- CN115304481A CN115304481A CN202210880518.3A CN202210880518A CN115304481A CN 115304481 A CN115304481 A CN 115304481A CN 202210880518 A CN202210880518 A CN 202210880518A CN 115304481 A CN115304481 A CN 115304481A
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- dimethyl
- malonate
- reaction
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- preparation
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- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 title claims abstract description 19
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 title claims abstract description 15
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- 238000006243 chemical reaction Methods 0.000 claims abstract description 23
- 239000002585 base Substances 0.000 claims abstract description 12
- BEPAFCGSDWSTEL-UHFFFAOYSA-N dimethyl malonate Chemical compound COC(=O)CC(=O)OC BEPAFCGSDWSTEL-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000007810 chemical reaction solvent Substances 0.000 claims abstract description 8
- 150000001335 aliphatic alkanes Chemical class 0.000 claims abstract description 6
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 5
- 238000006053 organic reaction Methods 0.000 claims abstract description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims abstract description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000003513 alkali Substances 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 3
- 239000003054 catalyst Substances 0.000 claims abstract description 3
- 239000011591 potassium Chemical group 0.000 claims abstract description 3
- 229910052700 potassium Chemical group 0.000 claims abstract description 3
- 239000011734 sodium Substances 0.000 claims abstract description 3
- 229910052708 sodium Inorganic materials 0.000 claims abstract description 3
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 19
- 239000000706 filtrate Substances 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 11
- 239000012043 crude product Substances 0.000 claims description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical group [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 4
- 150000002367 halogens Chemical group 0.000 claims description 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 238000001704 evaporation Methods 0.000 claims description 2
- 238000001914 filtration Methods 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 239000011630 iodine Substances 0.000 claims description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 2
- 239000003444 phase transfer catalyst Substances 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 230000002194 synthesizing effect Effects 0.000 abstract description 2
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 230000036632 reaction speed Effects 0.000 abstract 1
- 239000000047 product Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 150000001350 alkyl halides Chemical class 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 229920000547 conjugated polymer Polymers 0.000 description 3
- 239000012065 filter cake Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- LSXKDWGTSHCFPP-UHFFFAOYSA-N 1-bromoheptane Chemical compound CCCCCCCBr LSXKDWGTSHCFPP-UHFFFAOYSA-N 0.000 description 2
- MNDIARAMWBIKFW-UHFFFAOYSA-N 1-bromohexane Chemical compound CCCCCCBr MNDIARAMWBIKFW-UHFFFAOYSA-N 0.000 description 2
- VMKOFRJSULQZRM-UHFFFAOYSA-N 1-bromooctane Chemical compound CCCCCCCCBr VMKOFRJSULQZRM-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- -1 dimethyl 2, 2-diheptylmalonate Chemical compound 0.000 description 1
- WUXHROCHHBXGDN-UHFFFAOYSA-N dimethyl 2,2-dihexylpropanedioate Chemical compound CCCCCCC(C(=O)OC)(C(=O)OC)CCCCCC WUXHROCHHBXGDN-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229920001002 functional polymer Polymers 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
- C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
Abstract
The invention discloses a preparation method of dialkyl dimethyl malonate, which comprises the following steps: reacting dimethyl malonate and 1-halogenated alkane in an organic reaction solvent by taking alkali as a catalyst to prepare dimethyl dialkyl malonate, wherein the reaction formula is as follows:
Description
Technical Field
The invention relates to the technical field of organic synthesis, and particularly relates to a preparation method of dimethyl dialkyl malonate.
Background
Dimethyl dialkyl malonate is an important organic functional material intermediate, and the structural formula of the dimethyl dialkyl malonate is as follows:
organic functional polymers have been recognized as a new class of functional materials for their rich functional properties. From small molecules to macromolecules, the optical, electrical, magnetic and other properties of the polymer are more and more obvious. In order to ensure good solubility and solution processability of the organic conjugated polymer, a solubilizing group needs to be introduced on an aromatic unit in a polymer structure to increase the solubility of the organic conjugated polymer, so that the mobility of a current carrier in the organic conjugated polymer is influenced, and the performance of an organic functional material is correspondingly influenced. In the preparation of U.S. Pat. No. 5856569, U.S. Pat. application Nos. 20060148722 and 20050215488, a large excess of alkyl halide is used, raw materials are wasted greatly, the production cost is increased, and the post-treatment of the excess alkyl halide is complicated, which affects the product quality and yield. Moreover, DMF is used as a solvent in the reaction, the boiling point of DMF is high, DMF is difficult to remove by rotary evaporation after the reaction is finished, a large amount of water is needed for washing, the reaction cost is increased, and the product quality is influenced. The reaction time required for the above reaction is long, and at least 20 hours are required.
Disclosure of Invention
In view of the above technical problems in the related art, the present invention provides a method for preparing dimethyl dialkyl malonate, which can overcome the above disadvantages in the prior art.
In order to achieve the technical purpose, the technical scheme of the invention is realized as follows:
a method for preparing dimethyl dialkmalonate comprising the steps of:
reacting dimethyl malonate and 1-halogenated alkane in an organic reaction solvent by taking alkali as a catalyst to prepare dimethyl dialkyl malonate, wherein the reaction formula is as follows:
wherein n is an integer selected from 1 to 18, x is halogen, the base is MO-R, wherein R is a straight or branched chain alkane of 1 to 4 carbon atoms, and M is sodium or potassium.
Preferably, the base is sodium methoxide, sodium ethoxide, sodium tert-butoxide or potassium tert-butoxide.
Preferably, the organic reaction solvent is methanol, ethanol, n-butanol or t-butanol.
Preferably, the halogen is chlorine, bromine or iodine.
Preferably, the molar ratio of the dimethyl malonate to the 1-haloalkane is 1 (2-5).
Preferably, the molar ratio of the dimethyl malonate to the base is 1 (2-5).
Preferably, the molar ratio of the 1-haloalkane to the base is 1.
The preparation method of the dimethyl dialkyl malonate further comprises the following steps:
and filtering the prepared reaction product, collecting filtrate and evaporating to dryness to obtain a crude product of the dimethyl dialkyl malonate.
The invention has the beneficial effects that: the preparation method of the dimethyl dialkyl malonate is carried out in an organic homogeneous system, a phase transfer catalyst is not required to be added, the reaction and post-treatment steps are simplified, the reaction can be completed within 8 hours, the reaction time is shortened, the reaction efficiency is improved, and the production cost is reduced. In addition, the method greatly reduces the consumption of the alkyl halide in the reaction, so that excessive alkyl halide does not need to be removed by distillation after the reaction is finished, the post-treatment step is simplified, and the method is suitable for synthesizing an intermediate of an organic synthetic compound. The product obtained by the method has high yield which can reach more than 90 percent, and the reaction product can be directly used in the next reaction, thereby reducing the production cost and being suitable for industrial production.
Detailed Description
The technical solutions in the embodiments of the present invention will be described clearly and completely below, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments that can be derived by one of ordinary skill in the art from the embodiments given herein are intended to be within the scope of the present invention.
In the following examples, the yield is calculated as: (actual product mass/theoretical product mass) x 100%; eq is molar equivalent.
Example 1
Preparing dimethyl 2, 2-dihexylmalonate by taking potassium tert-butoxide as a base and tert-butanol as a reaction solvent:
50mL of tert-butanol was added to a 500mL three-necked flask, 10g of dimethyl malonate (0.075mol, 1.0eq), 13.7g of bromohexane (0.083mol, 1.1eq), 9.3g of potassium tert-butoxide (0.083mol, 1.1eq) were added with stirring, the mixture was heated to reflux, after 3 hours, 13.7g of bromohexane (0.83mol, 1.1eq) and 9.3g of potassium tert-butoxide (0.083mol, 1.1eq) were added, after 3 hours, a sample was taken to detect completion of the reaction, the reaction was cooled to room temperature and filtered, the filter cake was washed with 50mL of petroleum ether, the filtrates were combined, washed twice with water (50 mL. Times.2), twice with a saturated sodium chloride aqueous solution (50 mL. Times.2), dried over anhydrous sodium sulfate, the filtrate was spin-dried to give 20.7g of crude product, yield of 92%, and the product was used directly in the next reaction without further purification.
Example 2
Preparing dimethyl 2, 2-diheptylmalonate by taking potassium tert-butoxide as a base and tert-butanol as a reaction solvent:
50mL of tert-butyl alcohol is added into a 500mL three-necked bottle, 10g of dimethyl malonate (0.075mol, 1.0eq), 14.8g of bromoheptane (0.083mol, 1.1eq) and 9.3g of potassium tert-butoxide (0.083mol, 1.1eq) are added under stirring, the temperature is increased to reflux, 14.8g of bromoheptane (0.83mol, 1.1eq) and 9.3g of potassium tert-butoxide (0.083mol, 1.1eq) are added after 3 hours, TLC is carried out to detect complete reaction after 3 hours, the reaction is reduced to room temperature and then is filtered, 50mL of petroleum ether is used for washing a filter cake, the filtrate is combined, the filtrate is washed twice by water (50 mL multiplied by 2), the filtrate is washed twice by saturated sodium chloride aqueous solution (50 mL multiplied by 2), anhydrous sodium sulfate is dried, the filtrate is dried to obtain 22.4g of crude product, the crude product yield is 91%, and the crude product can be directly used for the next reaction without further purification.
Example 3
Preparing dimethyl 2, 2-dioctyl malonate by taking potassium tert-butoxide as a base and tert-butyl alcohol as a reaction solvent:
50mL of tert-butyl alcohol is added into a 500mL three-necked bottle, 10g of dimethyl malonate (0.075mol, 1.0eq), 16.1g of bromooctane (0.083mol, 1.1eq) and 9.3g of potassium tert-butoxide (0.083mol, 1.1eq) are added under stirring, the temperature is raised to reflux, 16.1g of bromooctane (0.83mol, 1.1eq) and 9.3g of potassium tert-butoxide (0.083mol, 1.1eq) are added after 3 hours, TLC is carried out for detecting complete reaction, the reaction is reduced to room temperature and then is carried out by suction filtration, 50mL petroleum ether is used for washing a filter cake, the filtrate is combined, the filtrate is washed twice (50 mL multiplied by 2) by water, the filtrate is washed twice (50 mL multiplied by 2) by saturated sodium chloride solution, anhydrous sodium sulfate is dried, the filtrate is dried by spin-drying to obtain 24.3g of crude product, the yield of the crude product is 91%, and the product can be directly used for the next reaction without further purification.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents, improvements and the like that fall within the spirit and principle of the present invention are intended to be included therein.
Claims (8)
1. The preparation method of dimethyl dialkyl malonate is characterized by comprising the following steps:
reacting dimethyl malonate and 1-halogenated alkane in an organic reaction solvent by taking alkali as a catalyst to prepare dimethyl dialkyl malonate, wherein the reaction formula is as follows:
wherein n is an integer selected from 1 to 18, x is halogen, the base is MO-R, wherein R is a straight or branched chain alkane of 1 to 4 carbon atoms, and M is sodium or potassium.
2. The method according to claim 1, wherein the base is sodium methoxide, sodium ethoxide, sodium tert-butoxide, or potassium tert-butoxide.
3. The method of claim 1, wherein the organic reaction solvent is methanol, ethanol, n-butanol, or t-butanol.
4. The method according to claim 1, wherein the halogen is chlorine, bromine or iodine.
5. The method according to claim 1, wherein the molar ratio of the dimethyl malonate to the 1-haloalkane is 1 (2-5).
6. The method according to claim 1, wherein the molar ratio of the dimethyl malonate to the base is 1 (2-5).
7. The method of producing dimethyl dialkylmalonate according to claim 1, characterized in that the molar ratio of the 1-haloalkane to the base is 1.
8. The method of producing dimethyl dialkylmalonate according to any one of claims 1 to 7, further comprising:
and filtering the prepared reaction product, collecting the filtrate and evaporating to dryness to obtain a crude product of the dimethyl dialkyl malonate.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210880518.3A CN115304481A (en) | 2022-07-25 | 2022-07-25 | Preparation method of dimethyl dialkyl malonate |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210880518.3A CN115304481A (en) | 2022-07-25 | 2022-07-25 | Preparation method of dimethyl dialkyl malonate |
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| Publication Number | Publication Date |
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| CN115304481A true CN115304481A (en) | 2022-11-08 |
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| CN202210880518.3A Withdrawn CN115304481A (en) | 2022-07-25 | 2022-07-25 | Preparation method of dimethyl dialkyl malonate |
Country Status (1)
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102241582A (en) * | 2010-05-10 | 2011-11-16 | 山东方明药业股份有限公司 | Synthesis technology of sodium valproate |
| CN103183612A (en) * | 2011-12-30 | 2013-07-03 | 北大方正集团有限公司 | Dipropylmalonic acid diester preparation method |
-
2022
- 2022-07-25 CN CN202210880518.3A patent/CN115304481A/en not_active Withdrawn
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102241582A (en) * | 2010-05-10 | 2011-11-16 | 山东方明药业股份有限公司 | Synthesis technology of sodium valproate |
| CN103183612A (en) * | 2011-12-30 | 2013-07-03 | 北大方正集团有限公司 | Dipropylmalonic acid diester preparation method |
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Application publication date: 20221108 |
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