CN116589442A - Preparation method of sesamol - Google Patents
Preparation method of sesamol Download PDFInfo
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- CN116589442A CN116589442A CN202310600136.5A CN202310600136A CN116589442A CN 116589442 A CN116589442 A CN 116589442A CN 202310600136 A CN202310600136 A CN 202310600136A CN 116589442 A CN116589442 A CN 116589442A
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- sesamol
- piperonyl
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- molar ratio
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- LUSZGTFNYDARNI-UHFFFAOYSA-N Sesamol Natural products OC1=CC=C2OCOC2=C1 LUSZGTFNYDARNI-UHFFFAOYSA-N 0.000 title claims abstract description 55
- UIOFUWFRIANQPC-JKIFEVAISA-N Floxacillin Chemical compound N([C@@H]1C(N2[C@H](C(C)(C)S[C@@H]21)C(O)=O)=O)C(=O)C1=C(C)ON=C1C1=C(F)C=CC=C1Cl UIOFUWFRIANQPC-JKIFEVAISA-N 0.000 title claims abstract description 53
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- ODQPZHOXLYATLC-UHFFFAOYSA-N 5-chloro-1,3-benzodioxole Chemical compound ClC1=CC=C2OCOC2=C1 ODQPZHOXLYATLC-UHFFFAOYSA-N 0.000 claims abstract description 18
- 125000004591 piperonyl group Chemical group C(C1=CC=2OCOC2C=C1)* 0.000 claims abstract description 18
- 229960005235 piperonyl butoxide Drugs 0.000 claims abstract description 17
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000000460 chlorine Substances 0.000 claims abstract description 11
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 11
- 239000000047 product Substances 0.000 claims abstract description 11
- 239000012043 crude product Substances 0.000 claims abstract description 8
- 238000000034 method Methods 0.000 claims abstract description 8
- 239000003054 catalyst Substances 0.000 claims abstract description 4
- 239000003513 alkali Substances 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 18
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 12
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 claims description 10
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical group [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- 238000005904 alkaline hydrolysis reaction Methods 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 230000020477 pH reduction Effects 0.000 claims description 6
- 239000003208 petroleum Substances 0.000 claims description 6
- 239000007810 chemical reaction solvent Substances 0.000 claims description 4
- 238000007670 refining Methods 0.000 claims description 4
- 238000005286 illumination Methods 0.000 claims description 3
- 239000002585 base Substances 0.000 claims description 2
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 238000001953 recrystallisation Methods 0.000 claims description 2
- 239000007858 starting material Substances 0.000 abstract description 7
- 238000009776 industrial production Methods 0.000 abstract description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- 238000004128 high performance liquid chromatography Methods 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 230000001105 regulatory effect Effects 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 3
- 238000005660 chlorination reaction Methods 0.000 description 3
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 239000008159 sesame oil Substances 0.000 description 2
- 235000011803 sesame oil Nutrition 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 238000005863 Friedel-Crafts acylation reaction Methods 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000007805 chemical reaction reactant Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 238000006400 oxidative hydrolysis reaction Methods 0.000 description 1
- 238000010979 pH adjustment Methods 0.000 description 1
- MXXWOMGUGJBKIW-YPCIICBESA-N piperine Chemical compound C=1C=C2OCOC2=CC=1/C=C/C=C/C(=O)N1CCCCC1 MXXWOMGUGJBKIW-YPCIICBESA-N 0.000 description 1
- 229940075559 piperine Drugs 0.000 description 1
- WVWHRXVVAYXKDE-UHFFFAOYSA-N piperine Natural products O=C(C=CC=Cc1ccc2OCOc2c1)C3CCCCN3 WVWHRXVVAYXKDE-UHFFFAOYSA-N 0.000 description 1
- 235000019100 piperine Nutrition 0.000 description 1
- SATCULPHIDQDRE-UHFFFAOYSA-N piperonal Chemical compound O=CC1=CC=C2OCOC2=C1 SATCULPHIDQDRE-UHFFFAOYSA-N 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to atoms of the carbocyclic ring
- C07D317/64—Oxygen atoms
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0215—Sulfur-containing compounds
- B01J31/0217—Mercaptans or thiols
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
The invention relates to a preparation method of sesamol, which specifically comprises the following steps: the piperonyl is reacted with chlorine to obtain 3, 4-methylenedioxy chlorobenzene under the action of a catalyst, the 3, 4-methylenedioxy chlorobenzene is hydrolyzed and acidified by alkali to obtain a sesamol crude product, and the crude product is refined to obtain a sesamol finished product. The preparation method of sesamol has the advantages of low cost and easy acquisition of starting materials, simple operation of the technological process, high yield, low cost and less three wastes, and is suitable for industrial production.
Description
Technical Field
The invention belongs to the technical field of chemical synthesis, and particularly relates to a preparation method of sesamol.
Background
Sesamol (Sesamol), also known as 3, 4-methylenedioxyphenol, named 3,4- (methyl) phenol, is present in sesame oil in very little amount, is a major aroma component and quality stabilizer of sesame oil, has excellent antibacterial and antioxidant activities, and is an excellent nontoxic antioxidant.
The literature reports that the chemical synthesis method of sesamol mainly comprises the following steps:
1) Taking piperine as a reaction starting material, and diazotizing and hydrolyzing to obtain sesamol:
2) Taking catechol as a starting material, and obtaining sesamol through cyclization, acetylation and oxidative hydrolysis:
3) Taking heliotropin as a starting material, and oxidizing to obtain sesamol:
4) Taking piperonyl as a starting material, and carrying out Friedel-crafts acylation, oxidation and hydrolysis to obtain sesamol:
5) Using hydroquinone as a starting material, and performing chlorination, hydrolysis and cyclization to obtain sesamol:
the synthesis method has the problems of high price of starting materials, low reaction yield, more three wastes and the like, and finally causes higher production cost and lacks market competitiveness. Therefore, a sesamol preparation method with low cost, high yield, good product quality and less three wastes is needed, and the method is suitable for industrial production.
Disclosure of Invention
Aiming at overcoming the defects of the prior art, the invention provides the preparation method of sesamol, which has the advantages of low cost, high yield, good product quality and less three wastes, and is suitable for industrial production.
In order to achieve the above purpose, the present invention adopts the following technical scheme:
a preparation method of sesamol comprises the following steps:
(1) The piperonyl and chlorine react in a reaction solvent at 10-50 ℃ under the condition of illumination to obtain 3, 4-methylenedioxy chlorobenzene, wherein the catalyst is iron powder and diphenyl sulfide;
(2) The 3, 4-methylenedioxy chlorobenzene in the step (1) is subjected to alkaline hydrolysis and acidification at the temperature of 10-50 ℃ to obtain sesamol crude product;
(3) Refining the sesamol crude product to obtain a sesamol finished product;
the chemical reaction formula is shown as formula I:
preferably, the molar ratio of piperonyl loop to chlorine in step (1) is 1 (1-10).
It is further preferred that the molar ratio of piperonyl loop to chlorine in step (1) is 1 (2-4).
It is further preferred that the temperature of the reaction in step (1) is 20 to 40 ℃.
Preferably, the molar ratio of the piperonyl loop to the diphenyl sulfide in the step (1) is 1 (0.001-0.01).
It is further preferred that the molar ratio of piperonyl loop to diphenyl sulfide in step (1) is 1 (0.005-0.008).
Preferably, the reaction solvent in the step (1) is at least one of carbon tetrachloride and carbon disulfide, and more preferably carbon tetrachloride.
Preferably, the reaction time in step (1) is 2 to 4 hours.
Preferably, the alkali in the step (2) is at least one selected from sodium hydroxide and potassium hydroxide.
Preferably, the molar ratio of the 3, 4-methylenedioxy chlorobenzene to the base in the step (2) is 1:1-5; more preferably 1:2 to 3.
Preferably, the acidification in step (2) is a pH adjustment with 20% sulfuric acid to a pH of 2 to 3; the alkaline hydrolysis time is 1-3 hours.
Preferably, in the step (2), the 3, 4-methylenedioxy chlorobenzene is subjected to alkaline hydrolysis and acidification at 20-30 ℃ to obtain a sesamol crude product.
Preferably, the refining in step (3) is recrystallisation from petroleum ether.
Compared with the prior art, the invention has the following technical effects:
(1) According to the invention, the piperonyl is selected as a starting material, sesamol is prepared by adopting a scheme of first chlorination and then hydrolysis, and the reaction of the piperonyl and chlorine gas chlorination uses iron powder/diphenyl sulfide as a catalyst, so that the yield can be greatly improved, and the generation of byproducts is reduced.
(2) The sesamol finished product prepared by the invention has low cost, high yield, good product quality and less three wastes, and is suitable for industrial production.
Drawings
FIG. 1 is a graph showing the results of HPLC analysis of sesamol obtained in example 1;
FIG. 2 is a graph showing the results of HPLC analysis of sesamol obtained in example 2;
FIG. 3 is a graph showing the results of HPLC analysis of sesamol obtained in comparative example 1;
FIG. 4 is a graph showing the results of HPLC analysis of sesamol obtained in comparative example 2.
Detailed Description
The present invention will be described in further detail with reference to the following specific examples, but the scope of the present invention is not limited thereto, and all techniques realized based on the above description of the present invention are within the scope of the present invention.
Example 1
(1) The reaction flask was charged with piperonyl (61 g,0.5 mol), carbon tetrachloride 200ml, iron powder 1g, diphenyl sulfide (0.75 g, 0.004mol), and chlorine (71 g,1.0 mol) was slowly introduced under stirring under light conditions, and reacted at 20 to 30℃for about 3 hours. After the reaction was completed, nitrogen was introduced, the mixture was filtered, and the solvent was distilled off from the filtrate under reduced pressure to obtain 75.9g of 3, 4-methylenedioxychlorobenzene as an oil, with a yield of 97% and a purity of 99% (GC).
(2) Sodium hydroxide (32 g,0.8 mol) was added to the reaction flask, 300ml of water was added thereto, and after dissolution by stirring, 3, 4-methylenedioxychlorobenzene (63 g,0.4 mol) was added thereto, followed by hydrolysis by stirring at 20 to 30℃for 2 hours. After the reaction is completed, regulating the pH to 2-3 by using 20% sulfuric acid, extracting by using dichloromethane, and evaporating the organic phase under reduced pressure to obtain a crude sesamol product.
(3) The crude sesamol is recrystallized by petroleum ether to obtain 52g of white crystalline powder sesamol with the yield of 94 percent and the purity of 99.52 percent (HPLC), and the analysis result of the HPLC is shown in figure 1.
Example 2
(1) The reaction flask was charged with piperonyl (61 g,0.5 mol) carbon disulphide 240ml, iron powder 0.6g, diphenyl sulfide (0.47 g,0.0025 mol) and under illumination, chlorine (107 g,1.5 mol) was slowly introduced under stirring to react for about 3 hours at 30-40 ℃. After the reaction was completed, nitrogen was introduced, the mixture was filtered, and the solvent was distilled off from the filtrate under reduced pressure to obtain 76.6g of 3, 4-methylenedioxychlorobenzene as an oil, with a yield of 98% and a purity of 99% (GC).
(2) Sodium hydroxide (48 g,1.2 mol) was added to the reaction flask, 450ml of water was added thereto, 3, 4-methylenedioxychlorobenzene (63 g,0.4 mol) was dissolved by stirring, and the mixture was hydrolyzed at 20 to 30℃for 2 hours by stirring. After the reaction is completed, regulating the pH to 2-3 by using 20% sulfuric acid, extracting by using dichloromethane, separating liquid, and evaporating an organic phase under reduced pressure to obtain a crude sesamol product.
(3) The crude sesamol is recrystallized by petroleum ether to obtain 51.5g of white crystalline powder sesamol, the yield is 93%, the purity is 99.74% (HPLC), and the analysis result of HPLC is shown in figure 2.
Comparative example 1
(1) A reaction flask was charged with 200ml of piperonyl (61 g,0.5 mol) carbon tetrachloride and 1g of iron powder, and chlorine (107 g,1.5 mol) was slowly introduced under stirring under light conditions, and reacted at 30 to 40℃for about 3 hours. After the reaction was completed, nitrogen was introduced, the mixture was filtered, and the solvent was distilled off from the filtrate under reduced pressure to obtain 68g of 3, 4-methylenedioxychlorobenzene as an oil, with a yield of 87% and a purity of 92% (GC).
(2) Sodium hydroxide (48 g,1.2 mol) was added to the reaction flask, 450ml of water was added thereto, 3, 4-methylenedioxychlorobenzene (63 g,0.4 mol) was dissolved by stirring, and the mixture was hydrolyzed at 20 to 30℃for 2 hours by stirring. After the reaction is completed, regulating the pH to 2-3 by using 20% sulfuric acid, extracting by using dichloromethane, separating liquid, and evaporating an organic phase under reduced pressure to obtain a crude sesamol product.
(3) The crude product was recrystallized from petroleum ether to give 45g of sesamol as an off-white crystalline powder in 81% yield and 96.46% purity (HPLC) with the analytical results shown in FIG. 3.
Comparative example 2
(1) The reaction flask was charged with piperonyl (61 g,0.5 mol), carbon tetrachloride 200ml, iron powder 1g, diphenyl sulfide (0.074 g,0.0004 mol), and under light conditions, chlorine (71 g,1.0 mol) was slowly introduced under stirring to react at 20 to 30℃for about 3 hours. After the reaction was completed, nitrogen was introduced, the mixture was filtered, and the solvent was distilled off from the filtrate under reduced pressure to obtain 69.6g of 3, 4-methylenedioxychlorobenzene as an oil, 89% yield and 95% purity (GC).
(2) Sodium hydroxide (32 g,0.8 mol) was added to the reaction flask, 300ml of water was added thereto, and after dissolution by stirring, 3, 4-methylenedioxychlorobenzene (63 g,0.4 mol) was added thereto, followed by hydrolysis by stirring at 20 to 30℃for 2 hours. After the reaction is completed, regulating the pH to 2-3 by using 20% sulfuric acid, extracting by using dichloromethane, and evaporating the organic phase under reduced pressure to obtain a crude sesamol product.
(3) The crude sesamol is recrystallized by petroleum ether to obtain 48g of white crystalline powder sesamol, the yield is 87%, the purity is 97.39% (HPLC), and the analysis result of the HPLC is shown in figure 4.
Claims (10)
1. The preparation method of sesamol is characterized by comprising the following steps:
(1) The piperonyl and chlorine react in a reaction solvent at 10-50 ℃ under the condition of illumination to obtain 3, 4-methylenedioxy chlorobenzene, wherein the catalyst is iron powder and diphenyl sulfide;
(2) The 3, 4-methylenedioxy chlorobenzene in the step (1) is subjected to alkaline hydrolysis and acidification at the temperature of 10-50 ℃ to obtain sesamol crude product;
(3) Refining the sesamol crude product to obtain a sesamol finished product;
the chemical reaction formula is shown as formula I:
2. the method for producing sesamol according to claim 1, wherein the molar ratio of piperonyl to chlorine in the step (1) is 1 (1-10); preferably, the molar ratio of the piperonyl loop to the chlorine in the step (1) is 1 (2-4); preferably, the temperature of the reaction in step (1) is 20 to 40 ℃.
3. The method for producing sesamol according to claim 1, wherein the molar ratio of the piperonyl ring to the diphenyl sulfide in the step (1) is 1 (0.001-0.01); preferably, the molar ratio of the piperonyl loop to the diphenyl sulfide in the step (1) is 1 (0.005-0.008).
4. The method for producing sesamol according to claim 1, wherein the reaction solvent in step (1) is at least one of carbon tetrachloride and carbon disulfide, preferably carbon tetrachloride.
5. The process for producing sesamol according to claim 1, wherein the reaction time in the step (1) is 2 to 4 hours.
6. The process for producing sesamol according to claim 1, wherein the alkali in the step (2) is at least one selected from the group consisting of sodium hydroxide and potassium hydroxide.
7. The method for producing sesamol according to claim 1, wherein the molar ratio of 3, 4-methylenedioxychlorobenzene to base in step (2) is 1:1 to 5; more preferably 1:2 to 3.
8. The process for producing sesamol according to claim 1, wherein the acidification in the step (2) is to adjust the pH to 2 to 3 with 20% sulfuric acid; the alkaline hydrolysis time is 1-3 hours.
9. The process for preparing sesamol according to claim 1, wherein the 3, 4-methylenedioxy chlorobenzene obtained in the step (2) is subjected to alkaline hydrolysis and acidification at 20 to 30 ℃ to obtain crude sesamol.
10. The method of producing sesamol according to claim 1, wherein the refining in step (3) is recrystallization using petroleum ether.
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| CN202310600136.5A CN116589442A (en) | 2023-05-25 | 2023-05-25 | Preparation method of sesamol |
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| Application Number | Priority Date | Filing Date | Title |
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| CN202310600136.5A CN116589442A (en) | 2023-05-25 | 2023-05-25 | Preparation method of sesamol |
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Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH06345756A (en) * | 1993-06-03 | 1994-12-20 | Hokko Chem Ind Co Ltd | Production of sesamol |
| CN108473498A (en) * | 2015-12-22 | 2018-08-31 | 豪夫迈·罗氏有限公司 | Pyrazolo [1,5a] pyrimidine derivatives as IRAK4 conditioning agents |
| CN109970542A (en) * | 2019-04-16 | 2019-07-05 | 沈阳药科大学 | Application of the quebrachite in copper catalysis aryl halides hydrolysis |
| CN111253361A (en) * | 2020-04-07 | 2020-06-09 | 苏州敬业医药化工有限公司 | Preparation method of 3, 4-methylenedioxyphenol |
| CN113563301A (en) * | 2021-07-27 | 2021-10-29 | 绵阳三香汇生物科技有限公司 | Synthesis process of 3, 4-methylenedioxyphenol |
| CN113666903A (en) * | 2021-09-01 | 2021-11-19 | 重庆化工职业学院 | Preparation method of sesamol |
-
2023
- 2023-05-25 CN CN202310600136.5A patent/CN116589442A/en active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH06345756A (en) * | 1993-06-03 | 1994-12-20 | Hokko Chem Ind Co Ltd | Production of sesamol |
| CN108473498A (en) * | 2015-12-22 | 2018-08-31 | 豪夫迈·罗氏有限公司 | Pyrazolo [1,5a] pyrimidine derivatives as IRAK4 conditioning agents |
| CN109970542A (en) * | 2019-04-16 | 2019-07-05 | 沈阳药科大学 | Application of the quebrachite in copper catalysis aryl halides hydrolysis |
| CN111253361A (en) * | 2020-04-07 | 2020-06-09 | 苏州敬业医药化工有限公司 | Preparation method of 3, 4-methylenedioxyphenol |
| CN113563301A (en) * | 2021-07-27 | 2021-10-29 | 绵阳三香汇生物科技有限公司 | Synthesis process of 3, 4-methylenedioxyphenol |
| CN113666903A (en) * | 2021-09-01 | 2021-11-19 | 重庆化工职业学院 | Preparation method of sesamol |
Non-Patent Citations (1)
| Title |
|---|
| 杨武德主编: "有机化学", 28 February 2015, 中国医药科技出版社, pages: 170 - 172 * |
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