CN103880621B - The method of reducing of preparation 7-methoxy-2-tetralone - Google Patents
The method of reducing of preparation 7-methoxy-2-tetralone Download PDFInfo
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- CN103880621B CN103880621B CN201410136686.7A CN201410136686A CN103880621B CN 103880621 B CN103880621 B CN 103880621B CN 201410136686 A CN201410136686 A CN 201410136686A CN 103880621 B CN103880621 B CN 103880621B
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- China
- Prior art keywords
- methoxy
- tetralone
- dimethoxy
- naphthalene
- reducing
- Prior art date
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- XEAPZXNZOJGVCZ-UHFFFAOYSA-N 7-methoxy-3,4-dihydro-1h-naphthalen-2-one Chemical compound C1CC(=O)CC2=CC(OC)=CC=C21 XEAPZXNZOJGVCZ-UHFFFAOYSA-N 0.000 title claims abstract description 18
- 238000000034 method Methods 0.000 title claims abstract description 13
- 238000002360 preparation method Methods 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 12
- PPKHAIRFQKFMLE-UHFFFAOYSA-N 2,7-dimethoxynaphthalene Chemical compound C1=CC(OC)=CC2=CC(OC)=CC=C21 PPKHAIRFQKFMLE-UHFFFAOYSA-N 0.000 claims abstract description 10
- 238000010531 catalytic reduction reaction Methods 0.000 claims abstract description 10
- 230000001699 photocatalysis Effects 0.000 claims abstract description 10
- 239000003960 organic solvent Substances 0.000 claims abstract description 8
- 239000011941 photocatalyst Substances 0.000 claims abstract description 7
- 230000007062 hydrolysis Effects 0.000 claims abstract description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 3
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 claims abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 3
- 229910010413 TiO 2 Inorganic materials 0.000 claims description 2
- 239000002245 particle Substances 0.000 claims description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 abstract description 6
- 239000002351 wastewater Substances 0.000 abstract description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- 238000000605 extraction Methods 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 238000006722 reduction reaction Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000005286 illumination Methods 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000243 solution Substances 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
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
- C07C45/513—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an etherified hydroxyl group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/20—Preparation of ethers by reactions not forming ether-oxygen bonds by hydrogenation of carbon-to-carbon double or triple bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a kind of method of reducing preparing 7-methoxy-2-tetralone, by 2,7-dimethoxy-naphthalene dissolves in organic solvent, with nano-photocatalyst, by UV-irradiation, what make 2,7-dimethoxy-naphthalene by photo catalytic reduction is reduced to compound (1), and compound (1) hydrolysis obtains 7-methoxy-2-tetralone.The present invention's reducing process used route is simple, normal-temperature operation, do not use the sodium Metal 99.5 of high-risk, waste water few, and product 7-methoxy-2-tetralone yield is high, and yield reaches more than 85%.
Description
Technical field
The present invention relates to a kind of method of reducing preparing 7-methoxy-2-tetralone.
Background technology
In early stage traditional 7-methoxy-2-tetralone production technology, the reduction reaction of 2,7-dimethoxy-naphthalene needs to carry out with sodium Metal 99.5 under the low temperature of-78 DEG C, and processing condition require high, and operational path is complicated, and dangerous large, product yield is low, and product cost is higher.
Had patent report to improve above-mentioned reducing process afterwards, as added organic solvent, organic amine, but reduction temperature is still at-20 ~ 5 DEG C, and use sodium Metal 99.5, temperature is lower, bad realization, uses sodium Metal 99.5, operation and process all more dangerous.
Summary of the invention
The object of the present invention is to provide that a kind of operational path is simple, normal-temperature operation, need not be dangerous sodium Metal 99.5 reduction, the method for reducing of preparation 7-methoxy-2-tetralone that product yield is high.
Technical solution of the present invention is:
Prepare a method of reducing for 7-methoxy-2-tetralone, it is characterized in that: dissolved in organic solvent by 2,7-dimethoxy-naphthalene, with nano-photocatalyst, by UV-irradiation, what make 2,7-dimethoxy-naphthalene by photo catalytic reduction is reduced to compound (1),
Compound (1) hydrolysis obtains 7-methoxy-2-tetralone:
Organic solvent is methyl alcohol, ethanol or Virahol, and the weight ratio of organic solvent and 2,7-dimethoxy-naphthalene is (10-20): 1.
Nano-photocatalyst used is CdS, ZnO or TiO
2, particle diameter is 20-100nm, and the weight ratio of nano-photocatalyst and 2,7-dimethoxy-naphthalene is (0.2-1.0): 1.
Photo catalytic reduction temperature is 20-35 DEG C; The photo catalytic reduction time is 8-16 hour.
The present invention's reducing process used route is simple, normal-temperature operation, do not use the sodium Metal 99.5 of high-risk, waste water few, and product 7-methoxy-2-tetralone yield is high, and yield reaches more than 85%.
Below in conjunction with specific embodiment, the present invention is further described.
Embodiment
Embodiment 1:
In 100mL round tube type quartz glass reaction bottle, add 50g methyl alcohol, 4g2,7-dimethoxy-naphthalene, 2g median size is at the CdS of 30nm, and magnetic agitation, leads to nitrogen and get rid of oxygen, use 150w Hg lamp irradiation, carry out photo catalytic reduction reaction, reduction temperature is 20-35 DEG C, and the recovery time is 9 hours.Stop illumination, stop logical nitrogen.Reaction mixture is filtered, removes catalyzer.
By above-mentioned filtrate distillation removing solvent methanol, obtain compound (1).Mixed with dioxane by compound (1), regulate pH to be 1-3 with dilute hydrochloric acid, reflux is hydrolyzed 3 hours.Be neutral by saturated sodium bicarbonate aqueous solution adjust ph.Distillation, except desolventizing, is used petroleum ether extraction aqueous phase, extraction phase is steamed sherwood oil, obtain 7-methoxy-2-tetralone, yield 85%.
Embodiment 2:
In 100mL round tube type quartz glass reaction bottle, add 50g methyl alcohol, 4g2,7-dimethoxy-naphthalene, 1g median size is at the ZnO of 60nm, and magnetic agitation, leads to nitrogen and get rid of oxygen, use 150w Hg lamp irradiation, carry out photo catalytic reduction reaction, reduction temperature is 20-35 DEG C, and the recovery time is 12 hours.Stop illumination, stop logical nitrogen.Reaction mixture is filtered, removes catalyzer.
By above-mentioned filtrate distillation removing solvent methanol, obtain compound (1).Mixed with dioxane by compound (1), regulate pH to be 1-3 with dilute hydrochloric acid, reflux is hydrolyzed 3 hours.Be neutral by saturated sodium bicarbonate aqueous solution adjust ph.Distillation, except desolventizing, is used petroleum ether extraction aqueous phase, extraction phase is steamed sherwood oil, obtain 7-methoxy-2-tetralone, yield 85.3%.
Embodiment 3:
In 100mL round tube type quartz glass reaction bottle, add 50g ethanol (or Virahol), 4g2,7-dimethoxy-naphthalene, 2g median size is at the TiO of 50nm
2, magnetic agitation, logical nitrogen gets rid of oxygen, and use 150w Hg lamp irradiation, carry out photo catalytic reduction reaction, reduction temperature is 20-35 DEG C, and the recovery time is 15 hours.Stop illumination, stop logical nitrogen.Reaction mixture is filtered, removes catalyzer.
By above-mentioned filtrate distillation removing solvent methanol, obtain compound (1).Mixed with dioxane by compound (1), regulate pH to be 1-3 with dilute hydrochloric acid, reflux is hydrolyzed 3 hours.Be neutral by saturated sodium bicarbonate aqueous solution adjust ph.Distillation, except desolventizing, is used petroleum ether extraction aqueous phase, extraction phase is steamed sherwood oil, obtain 7-methoxy-2-tetralone, yield 85.6%.
Claims (3)
1. prepare a method of reducing for 7-methoxy-2-tetralone, it is characterized in that: 2,7-dimethoxy-naphthalene is dissolved in organic solvent, with nano-photocatalyst, by UV-irradiation, make 2 by photo catalytic reduction, 7-dimethoxy-naphthalene be reduced to compound (1)
Compound (1) hydrolysis obtains 7-methoxy-2-tetralone; Nano-photocatalyst used is CdS, ZnO or TiO
2, particle diameter is 20-100nm, and the weight ratio of nano-photocatalyst and 2,7-dimethoxy-naphthalene is (0.2-1.0): 1.
2. the method for reducing of preparation 7-methoxy-2-tetralone according to claim 1, it is characterized in that: organic solvent is methyl alcohol, ethanol or Virahol, the weight ratio of organic solvent and 2,7-dimethoxy-naphthalene is (10-20): 1.
3. the method for reducing of preparation 7-methoxy-2-tetralone according to claim 1, is characterized in that: photo catalytic reduction temperature is 20-35 DEG C; The photo catalytic reduction time is 8-16 hour.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410136686.7A CN103880621B (en) | 2014-04-04 | 2014-04-04 | The method of reducing of preparation 7-methoxy-2-tetralone |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410136686.7A CN103880621B (en) | 2014-04-04 | 2014-04-04 | The method of reducing of preparation 7-methoxy-2-tetralone |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN103880621A CN103880621A (en) | 2014-06-25 |
| CN103880621B true CN103880621B (en) | 2015-08-12 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201410136686.7A Active CN103880621B (en) | 2014-04-04 | 2014-04-04 | The method of reducing of preparation 7-methoxy-2-tetralone |
Country Status (1)
| Country | Link |
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| CN (1) | CN103880621B (en) |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003206253A (en) * | 2002-01-08 | 2003-07-22 | Kanegafuchi Chem Ind Co Ltd | Method for producing alkoxy-substituted 2-tetralone |
| CN1438210A (en) * | 2003-03-13 | 2003-08-27 | 南通莱嘉利化工有限公司 | 7-methoxy-2-telralin-one production method |
| CN1634862A (en) * | 2004-10-25 | 2005-07-06 | 天津大学 | Process for photo catalytic reduction preparation of p-chloroaniline |
| CN101468946A (en) * | 2007-12-25 | 2009-07-01 | 南通莱嘉利化工有限公司 | Preparation technique of 5-methoxy-2-tetralone |
-
2014
- 2014-04-04 CN CN201410136686.7A patent/CN103880621B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003206253A (en) * | 2002-01-08 | 2003-07-22 | Kanegafuchi Chem Ind Co Ltd | Method for producing alkoxy-substituted 2-tetralone |
| CN1438210A (en) * | 2003-03-13 | 2003-08-27 | 南通莱嘉利化工有限公司 | 7-methoxy-2-telralin-one production method |
| CN1634862A (en) * | 2004-10-25 | 2005-07-06 | 天津大学 | Process for photo catalytic reduction preparation of p-chloroaniline |
| CN101468946A (en) * | 2007-12-25 | 2009-07-01 | 南通莱嘉利化工有限公司 | Preparation technique of 5-methoxy-2-tetralone |
Non-Patent Citations (1)
| Title |
|---|
| 萘满酮类化合物的合成与制备方法;金浩等;《兰州理工大学学报》;20130831;第39卷(第4期);第70-73页 * |
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| CN103880621A (en) | 2014-06-25 |
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| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| CP01 | Change in the name or title of a patent holder |
Address after: 226221 No.1 Shanghai Road, Binjiang fine chemical industry park, Qidong City, Nantong City, Jiangsu Province Patentee after: Nantong Baisheng Pharmaceutical Co.,Ltd. Address before: 226221 No.1 Shanghai Road, Binjiang fine chemical industry park, Qidong City, Nantong City, Jiangsu Province Patentee before: NANTONG BAISHENG CHEMICAL Co.,Ltd. |
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| CP01 | Change in the name or title of a patent holder | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20221124 Address after: Room 820, Strategic Emerging Industry Incubation Base, Qinchuan Park, Lanzhou New Area, Lanzhou, Gansu 730311 Patentee after: Baisheng New Materials (Gansu) Co.,Ltd. Address before: 226221 No.1 Shanghai Road, Binjiang fine chemical industry park, Qidong City, Nantong City, Jiangsu Province Patentee before: Nantong Baisheng Pharmaceutical Co.,Ltd. |
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| TR01 | Transfer of patent right |