CN117603026A - Synthesis method of visible light induced anisaldehyde - Google Patents
Synthesis method of visible light induced anisaldehyde Download PDFInfo
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- CN117603026A CN117603026A CN202311609681.7A CN202311609681A CN117603026A CN 117603026 A CN117603026 A CN 117603026A CN 202311609681 A CN202311609681 A CN 202311609681A CN 117603026 A CN117603026 A CN 117603026A
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- visible light
- synthesizing
- anisaldehyde
- induced
- photocatalyst
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- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 title claims abstract description 61
- 238000001308 synthesis method Methods 0.000 title description 2
- MSHFRERJPWKJFX-UHFFFAOYSA-N 4-Methoxybenzyl alcohol Chemical compound COC1=CC=C(CO)C=C1 MSHFRERJPWKJFX-UHFFFAOYSA-N 0.000 claims abstract description 28
- 238000000034 method Methods 0.000 claims abstract description 24
- 238000006243 chemical reaction Methods 0.000 claims abstract description 18
- 230000002194 synthesizing effect Effects 0.000 claims abstract description 18
- 239000011941 photocatalyst Substances 0.000 claims abstract description 14
- 238000003756 stirring Methods 0.000 claims abstract description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000001301 oxygen Substances 0.000 claims abstract description 5
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- 239000002994 raw material Substances 0.000 claims description 9
- SEACYXSIPDVVMV-UHFFFAOYSA-L eosin Y Chemical compound [Na+].[Na+].[O-]C(=O)C1=CC=CC=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C([O-])=C(Br)C=C21 SEACYXSIPDVVMV-UHFFFAOYSA-L 0.000 claims description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 4
- 230000006698 induction Effects 0.000 claims description 3
- IICCLYANAQEHCI-UHFFFAOYSA-N 4,5,6,7-tetrachloro-3',6'-dihydroxy-2',4',5',7'-tetraiodospiro[2-benzofuran-3,9'-xanthene]-1-one Chemical compound O1C(=O)C(C(=C(Cl)C(Cl)=C2Cl)Cl)=C2C21C1=CC(I)=C(O)C(I)=C1OC1=C(I)C(O)=C(I)C=C21 IICCLYANAQEHCI-UHFFFAOYSA-N 0.000 claims description 2
- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 claims description 2
- 229930187593 rose bengal Natural products 0.000 claims description 2
- 229940081623 rose bengal Drugs 0.000 claims description 2
- STRXNPAVPKGJQR-UHFFFAOYSA-N rose bengal A Natural products O1C(=O)C(C(=CC=C2Cl)Cl)=C2C21C1=CC(I)=C(O)C(I)=C1OC1=C(I)C(O)=C(I)C=C21 STRXNPAVPKGJQR-UHFFFAOYSA-N 0.000 claims description 2
- 238000005286 illumination Methods 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 229910052723 transition metal Inorganic materials 0.000 description 3
- 150000003624 transition metals Chemical class 0.000 description 3
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical class COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- KMUONIBRACKNSN-UHFFFAOYSA-N potassium dichromate Chemical compound [K+].[K+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O KMUONIBRACKNSN-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000007790 solid phase Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- -1 20.0 mL) Chemical compound 0.000 description 1
- 235000014493 Crataegus Nutrition 0.000 description 1
- 241001092040 Crataegus Species 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 206010034703 Perseveration Diseases 0.000 description 1
- 244000068689 Pimpinella saxifraga Species 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000007336 electrophilic substitution reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000009322 erkang Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 239000003345 natural gas Substances 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 229910021654 trace metal Inorganic materials 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
- C07C45/37—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of >C—O—functional groups to >C=O groups
- C07C45/38—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of >C—O—functional groups to >C=O groups being a primary hydroxyl group
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention discloses a method for synthesizing visible light-induced anisaldehyde, which comprises the following steps: under the oxygen atmosphere, adding 4-methoxy benzyl alcohol and a photocatalyst into a reaction vessel equipped with a stirring device, adding an organic solvent, and stirring at room temperature under the irradiation of a 45W energy-saving lamp to obtain anisic aldehyde. The method is green in the whole process, efficient and easy to operate, and is a good method for synthesizing anisic aldehyde.
Description
Technical Field
The invention belongs to the technical field of catalytic chemistry, and particularly relates to application of high-efficiency synthesis of anisaldehyde by visible light induction.
Background
4-methoxybenzaldehyde is also called anisaldehyde, is colorless or light yellow liquid, has the fragrance of pimpinella and hawthorns, and is widely applied to the fields of medicine synthesis, perfume preparation, essence preparation and the like [ Wang Zhongdong, han Shuai, li Weimin ], shandong chemical industry, 2023, 52, 76]. Therefore, the market demand thereof increases year by year. In the teaching materials of organic chemistry of the family, sha Ruite reagent containing chromic anhydride and pyridine [ chen her perseveration, pei Weiwei, xu Ruiqiu, pei Jian ] basic organic chemistry fourth edition Beijing university press, 2017]Through research, in the teaching of the experiment of the family, the chromic anhydride is generatedAnd the relatively large toxicity of pyridine lacks such experiments, so that theoretical teaching and basic experiments are disjointed [ Sun Erkang, zhang Jianrong, cao Jian, guo Lingxiang. Organic chemistry experiments third edition. Nanjing: nanjing university Press, 2018; fu Chunling, chen Shizhong organic chemistry experiments, first edition, hangzhou, university of Zhejiang press, 2000]. At present, potassium dichromate oxidation reaction which is mainly divided into olefin is carried out according to the difference of raw materials for synthesizing anisaldehyde [ He Chunmao ], forest chemical industry communication, 2004, 38, 31]The electrophilic substitution of anisole is highly polluting [ Wang Chang. Natural gas chemical, 1990, 39, 46]Poor regioselectivity, high separation and purification requirements, p-hydroxybenzaldehyde methylation [ Xu Kexun. Handbook of Fine organic chemical raw materials and intermediates, first edition, beijing: chemical industry Press, 1998)]The dimethyl sulfate used belongs to organic drastic drugs. In recent years, transition metals have been usedNat. Commun. 2022, 13, 428]Biological enzyme [J. Am. Chem. Soc. 2023, 145, 4421]Solid phase catalystJ. Am. Chem. Soc. 2022, 144, 14090]And electrocatalysis [Nat. Commun. 2022, 13, 147]Can realize the synthesis of anisaldehyde. However, trace metal residues exist after the transition metal reaction, the preparation steps of biological enzymes and solid phase catalysts are complicated, and the hydrogen generated by electrocatalytic reaction has a great potential safety hazard.
Disclosure of Invention
In order to overcome the technical problems, the invention provides a method for efficiently synthesizing anisic aldehyde by utilizing visible light to induce the oxidation reaction of 4-methoxy benzyl alcohol under the condition of no transition metal catalyst. The method takes 4-methoxy benzyl alcohol as a raw material, dimethyl sulfoxide as a solvent, eosin Y as a photocatalyst, and realizes the efficient synthesis of anisic aldehyde under the irradiation of a 45W energy-saving lamp. In addition, the invention obtains anisaldehyde with higher yield. The whole catalytic process of the invention is green, efficient and easy to operate, and is a good method for synthesizing anisic aldehyde.
Specifically, the invention adopts the following technical scheme:
a method for synthesizing anisaldehyde by using visible light induction comprises the following steps of taking 4-methoxybenzyl alcohol as a raw material, and carrying out visible light irradiation reaction in the presence of a photocatalyst to obtain the anisaldehyde.
The invention discloses an application of 4-methoxy benzyl alcohol serving as a raw material in preparation of anisic aldehyde by visible light in the presence of a photocatalyst.
In the present invention, the photoreaction is performed in air or oxygen, preferably oxygen.
In the present invention, the photocatalyst is selected from any one of eosin Y, rose bengal and fluorescein, preferably eosin Y.
In the invention, the visible light irradiation reaction is carried out in a solvent; preferably, the solvent is selected fromN,NDimethylformamide (DMF), dimethyl sulfoxide (DMSO),NAny one of methyl pyrrolidone (NMP), acetonitrile (MeCN) and methanol (MeOH), preferably dimethyl sulfoxide (DMSO).
In the invention, the mol ratio between the 4-methoxybenzyl alcohol and the photocatalyst is 1 (0.01-0.1), and the preferable mol ratio is 1 (0.03-0.07).
In the present invention, the visible light reaction is carried out under stirring, and preferably, the stirring device is a magnetic stirring device.
In the invention, the visible light irradiation reaction is carried out under the irradiation of a 45W energy-saving lamp and stirred at room temperature. Preferably, in the above method for synthesizing anisaldehyde, the reaction time of the reaction is 1 to 5 hours.
Compared with the prior art, the invention adopting the technical scheme has the following advantages: according to the invention, 4-methoxybenzyl alcohol is used as a raw material for the first time, dimethyl sulfoxide is used as a solvent, eosin Y is used as a photocatalyst, and high-efficiency synthesis of anisaldehyde is realized under the irradiation of a 45W energy-saving lamp. In addition, the invention can obtain anisaldehyde with higher yield. The whole process is green, efficient and easy to operate, and is a good method for synthesizing anisic aldehyde.
Detailed Description
According to the invention, 4-methoxy benzyl alcohol is used as a raw material, dimethyl sulfoxide is used as a solvent, eosin Y is used as a photocatalyst, and high-efficiency synthesis of anisic aldehyde is realized under the irradiation of a 45W energy-saving lamp. In addition, the invention can obtain anisaldehyde with higher yield. The whole process is green, efficient and easy to operate, and is a good method for synthesizing anisic aldehyde.
As an example, the reaction mixture is added into a reaction vessel equipped with a stirring device according to the mol ratio of 4-methoxybenzyl alcohol to the photocatalyst of 1:0.05 under the oxygen atmosphere, and then 20 mL dimethyl sulfoxide (DMSO) is added, and the reaction mixture is stirred at room temperature for 3 hours under the irradiation of a 45W energy-saving lamp to obtain anisic aldehyde. The reaction is schematically as follows:
。
the invention will be further described with reference to specific examples. Reagents, materials, instruments, and the like used in the following examples are commercially available unless otherwise indicated. The specific operation method and the performance test adopted by the invention are conventional technologies.
Examples
To a 50 mL round bottom flask was added sequentially a magnetic stirrer, 4-methoxybenzyl alcohol (3.0 mmol,0.372 mL), dimethyl sulfoxide (DMSO, 20.0 mL), eosin Y (Eosin Y,0.1038 g), oxygen gas was introduced, stirring, the light source was turned on, and stirring 3 h. Monitoring the reaction by thin layer chromatography, wherein the volume ratio of the developing agent is as followsV Petroleum ether : V Acetic acid ethyl ester =5:1, the ratio shift value is about 0.5.
After the reaction was completed, 10.0. 10.0 mL deionized water was added to the round-bottomed flask to quench the reaction, the reaction solution was transferred to a 125 mL separating funnel, 20.0. 20.0 mL saturated brine was added, 15.0. 15.0 mL dichloromethane was added to extract, and the organic phase was collected and repeated three times. The organic phase was transferred to a separatory funnel, washed with 20.0. 20.0 mL saturated saline, repeated twice, washed with 30.0 mL deionized water, the organic phase was a yellow liquid, transferred to a 100 mL round bottom flask, decolorized with 1.0000 g activated carbon, and stirred for 10 min. The filtrate was filtered and collected as a colorless liquid. The filtrate was transferred to a 100 mL round bottom flask, 0.5000 g anhydrous magnesium sulfate was added and stirred for 15 min. Filtering and collecting filtrate. Vacuum distillation, weighing, and making anisic aldehyde into colorless liquid0.3717 g, the yield was 91%. 1 H NMR (400 MHz, CDCl 3 , ppm) δ = 9.78 (s, 1H), 7.79-7.67 (m, 2H), 6.97-6.85 (m, 2H), 3.78 (s, 3H). 13 C NMR (101 MHz, CDCl 3 Ppm) δ=190.8, 164.6, 131.9, 130.1, 129.8, 114.6, 114.5, 114.3, 113.9, 55.5. The characterization result proves that the product anisic aldehyde is obtained.
On the basis of examples, the conditions were changed to obtain the following results.
Claims (10)
1. A method for synthesizing anisic aldehyde by using visible light induction is characterized by comprising the following steps of taking 4-methoxybenzyl alcohol as a raw material, and carrying out visible light irradiation reaction in the presence of a photocatalyst to obtain the anisic aldehyde.
2. The method for synthesizing visible light-induced anisaldehyde according to claim 1, wherein the photoreaction is performed in air or oxygen.
3. The method for synthesizing visible light-induced anisaldehyde according to claim 1, wherein the photocatalyst is any one selected from eosin Y, rose bengal and fluorescein.
4. The method for synthesizing visible light-induced anisaldehyde according to claim 1, wherein the visible light reaction is performed in a solvent.
5. The method for synthesizing visible light-induced anisaldehyde according to claim 4, wherein the solvent is selected from the group consisting ofN,NDimethylformamide, dimethyl sulfoxide,N-any one of methyl pyrrolidone, acetonitrile, methanol.
6. The method for synthesizing visible light induced anisaldehyde according to claim 1, wherein the molar ratio between the 4-methoxybenzyl alcohol and the photocatalyst is 1 (0.01-0.1).
7. The method for synthesizing visible light induced anisaldehyde according to claim 6, wherein the molar ratio between the 4-methoxybenzyl alcohol and the photocatalyst is 1 (0.03-0.07).
8. The method for synthesizing visible light-induced anisaldehyde according to claim 1, wherein the visible light reaction is performed under stirring.
9. The method for synthesizing the visible light-induced anisaldehyde according to claim 1, wherein the visible light irradiation reaction is carried out under the irradiation of a 45W energy-saving lamp with stirring at room temperature.
10. 4-methoxy benzyl alcohol is used as a raw material and is applied to the preparation of anisic aldehyde by visible light illumination in the presence of a photocatalyst.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202311609681.7A CN117603026A (en) | 2023-11-29 | 2023-11-29 | Synthesis method of visible light induced anisaldehyde |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202311609681.7A CN117603026A (en) | 2023-11-29 | 2023-11-29 | Synthesis method of visible light induced anisaldehyde |
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| CN117603026A true CN117603026A (en) | 2024-02-27 |
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| CN202311609681.7A Pending CN117603026A (en) | 2023-11-29 | 2023-11-29 | Synthesis method of visible light induced anisaldehyde |
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| Country | Link |
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| CN (1) | CN117603026A (en) |
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- 2023-11-29 CN CN202311609681.7A patent/CN117603026A/en active Pending
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