AR089310A1 - Proceso para la preparacion de magnolol y derivados del mismo - Google Patents
Proceso para la preparacion de magnolol y derivados del mismoInfo
- Publication number
- AR089310A1 AR089310A1 ARP120104803A ARP120104803A AR089310A1 AR 089310 A1 AR089310 A1 AR 089310A1 AR P120104803 A ARP120104803 A AR P120104803A AR P120104803 A ARP120104803 A AR P120104803A AR 089310 A1 AR089310 A1 AR 089310A1
- Authority
- AR
- Argentina
- Prior art keywords
- biphenyl
- diol
- diallyl
- dimethoxy
- magnolol
- Prior art date
Links
- VVOAZFWZEDHOOU-UHFFFAOYSA-N magnolol Chemical compound OC1=CC=C(CC=C)C=C1C1=CC(CC=C)=CC=C1O VVOAZFWZEDHOOU-UHFFFAOYSA-N 0.000 title abstract 6
- 238000000034 method Methods 0.000 title abstract 3
- OYAQUBKYAKSHOA-UHFFFAOYSA-N 2-(2-hydroxy-5-propylphenyl)-4-propylphenol Chemical compound CCCC1=CC=C(O)C(C=2C(=CC=C(CCC)C=2)O)=C1 OYAQUBKYAKSHOA-UHFFFAOYSA-N 0.000 abstract 4
- DGZPCLLOAOYMPP-UHFFFAOYSA-N 2-phenyl-4,4-dipropylcyclohexa-2,5-diene-1,1-diol Chemical compound CCCC1(CCC)C=CC(O)(O)C(C=2C=CC=CC=2)=C1 DGZPCLLOAOYMPP-UHFFFAOYSA-N 0.000 abstract 3
- UZXJWBQKRATXHF-UHFFFAOYSA-N COC1(C(=CC(C=C1)(Br)Br)C1=CC=CC=C1)OC Chemical group COC1(C(=CC(C=C1)(Br)Br)C1=CC=CC=C1)OC UZXJWBQKRATXHF-UHFFFAOYSA-N 0.000 abstract 2
- GARRUKBUEWVRCV-UHFFFAOYSA-N [6-fluoro-1-[(2-methylpropan-2-yl)oxycarbonyl]indol-2-yl]boronic acid Chemical group C1=C(F)C=C2N(C(=O)OC(C)(C)C)C(B(O)O)=CC2=C1 GARRUKBUEWVRCV-UHFFFAOYSA-N 0.000 abstract 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 2
- 239000004305 biphenyl Substances 0.000 abstract 2
- 238000011084 recovery Methods 0.000 abstract 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 abstract 2
- MSVMSXHTHSWNAU-UHFFFAOYSA-N 2-phenylcyclohexa-2,4-diene-1,1-diol Chemical compound OC1(O)CC=CC=C1C1=CC=CC=C1 MSVMSXHTHSWNAU-UHFFFAOYSA-N 0.000 abstract 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 1
- 230000029936 alkylation Effects 0.000 abstract 1
- 238000005804 alkylation reaction Methods 0.000 abstract 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 abstract 1
- 235000010290 biphenyl Nutrition 0.000 abstract 1
- 230000031709 bromination Effects 0.000 abstract 1
- 238000005893 bromination reaction Methods 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 230000017858 demethylation Effects 0.000 abstract 1
- 238000010520 demethylation reaction Methods 0.000 abstract 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 230000011987 methylation Effects 0.000 abstract 1
- 238000007069 methylation reaction Methods 0.000 abstract 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/50—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions decreasing the number of carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/01—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
- C07C37/055—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis the substituted group being bound to oxygen, e.g. ether group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/001—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by modification in a side chain
- C07C37/003—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by modification in a side chain by hydrogenation of an unsaturated part
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/62—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by introduction of halogen; by substitution of halogen atoms by other halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
-
- 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
- C07C41/05—Preparation of ethers by addition of compounds to unsaturated compounds
- C07C41/06—Preparation of ethers by addition of compounds to unsaturated compounds by addition of organic compounds only
-
- 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
- C07C41/16—Preparation of ethers by reaction of esters of mineral or organic acids with hydroxy or O-metal groups
-
- 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
- C07C41/22—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of halogens; by substitution of halogen atoms by other halogen atoms
-
- 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
- C07C41/24—Preparation of ethers by reactions not forming ether-oxygen bonds by elimination of halogens, e.g. elimination of HCl
-
- 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
- C07C41/30—Preparation of ethers by reactions not forming ether-oxygen bonds by increasing the number of carbon atoms, e.g. by oligomerisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
En la presente se describen métodos de elevado rendimiento para la preparación de magnolol (5,5-dialil-bifenil-2,2-diol) y tetrahidromagnolol (5,5-dipropil-bifenil-2,2-diol). Reivindicación 1: Un método para la preparación de magnolol (5,5-dialil-bifenil-2,2-diol) o tetrahidromagnolol (5,5-dipropil-bifenil-2,2-diol), que comprende i) la metilación de bifenil-2,2-diol utilizando sulfato de dimetilo, para obtener 2,2-dimetoxi-bifenilo; ii) la bromuración del 2,2-dimetoxi-bifenilo para obtener 2,2-dimetoxi-5,5-dibromo-bifenilo; iii) la alquilación del 2,2-dimetoxi-5,5-dibromo-bifenilo con bromuro de alilo para obtener 2,2-dimetoxi-5,5-dialil-bifenilo; iv) la desmetilación del 2,2-dimetoxi-5,5-dialil-bifenilo mediante la reacción con cloruro de aluminio y tiourea; v) la recuperación del 5,5-dialil-bifenil-2,2-diol obtenido de esta forma; y vi) opcionalmente la hidrogenación del 5,5-dialil-bifenil-2,2-diol en presencia de un catalizador metálico y la recuperación del 5,5-dipropil-bifenil-2,2-diol obtenido de esta forma.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/US2011/066045 WO2013095361A1 (en) | 2011-12-20 | 2011-12-20 | Processes for making magnolol and derivatives thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR089310A1 true AR089310A1 (es) | 2014-08-13 |
Family
ID=45498119
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP120104803A AR089310A1 (es) | 2011-12-20 | 2012-12-18 | Proceso para la preparacion de magnolol y derivados del mismo |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US9000231B2 (es) |
| EP (1) | EP2794534B1 (es) |
| JP (1) | JP2015500874A (es) |
| CN (1) | CN103987684A (es) |
| AR (1) | AR089310A1 (es) |
| AU (1) | AU2011383722B2 (es) |
| BR (1) | BR112014014255A2 (es) |
| CA (1) | CA2858954A1 (es) |
| MX (1) | MX2014007555A (es) |
| PH (1) | PH12014501367A1 (es) |
| RU (1) | RU2014129826A (es) |
| SG (1) | SG11201402848YA (es) |
| TW (1) | TWI504585B (es) |
| WO (1) | WO2013095361A1 (es) |
| ZA (1) | ZA201404277B (es) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX351329B (es) | 2013-01-23 | 2017-10-11 | Colgate Palmolive Co | Proceso para elaborar derivados de magnolol. |
| CN105622603A (zh) * | 2015-05-28 | 2016-06-01 | 广州牌牌生物科技有限公司 | 多核化合物、其制备方法以及其应用 |
| CN109053387B (zh) * | 2018-09-19 | 2021-07-09 | 九江学院 | 一种厚朴酚的合成方法 |
| WO2020126347A1 (en) | 2018-12-18 | 2020-06-25 | Unilever N.V. | An antimicrobial composition |
| CN113717683B (zh) * | 2021-09-27 | 2023-05-09 | 武汉纺织大学 | 一种光固化水下生物基抗菌胶粘剂及其制备方法 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5959157A (en) * | 1995-06-26 | 1999-09-28 | Alliedsignal, Inc. | Process for making hydroxy-substituted ethynylated biphenyl compounds |
| CN1106391C (zh) | 1999-04-12 | 2003-04-23 | 李安荣 | 厚朴酚系列化合物及其合成方法和以该化合物为活性成分的药物组合物 |
| US6500409B1 (en) | 2000-05-10 | 2002-12-31 | Colgate Palmolive Company | Synergistic antiplaque/antigingivitis oral composition |
| JP4851940B2 (ja) | 2004-11-19 | 2012-01-11 | 宮城県 | がんまたは糖尿病治療のための医薬組成物 |
| WO2006061666A2 (en) | 2004-12-08 | 2006-06-15 | Richter Gedeon Vegyészeti Gyár Rt. | A new process for the preparation of phenolic hydroxy-substituted compounds |
| WO2006129898A1 (en) | 2005-05-30 | 2006-12-07 | Korea Institute Of Oriental Medicine | A mass separation method of magnolol from magnoliae cortex ormagnoliae radix |
| EP2040696B1 (en) | 2006-07-14 | 2017-01-25 | DSM IP Assets B.V. | Compositions and use thereof for the treatment, co-treatment or prevention of inflammatory disorders |
| CN101293816B (zh) | 2008-06-24 | 2011-09-28 | 江南大学 | 厚朴酚的合成方法 |
| JP5265282B2 (ja) * | 2008-09-19 | 2013-08-14 | 花王株式会社 | 皮膚化粧料 |
| TWI422382B (zh) | 2010-02-24 | 2014-01-11 | Colgate Palmolive Co | 加強木蘭活性物之溶解度及傳送的組成物 |
| TWI459957B (zh) | 2010-02-24 | 2014-11-11 | Colgate Palmolive Co | 口腔保健組成物 |
| US8519197B2 (en) | 2010-02-25 | 2013-08-27 | Colgate-Palmolive Company | Synthesis of magnolol and its analogue compounds |
-
2011
- 2011-06-20 US US14/365,791 patent/US9000231B2/en active Active
- 2011-12-20 BR BR112014014255A patent/BR112014014255A2/pt not_active IP Right Cessation
- 2011-12-20 WO PCT/US2011/066045 patent/WO2013095361A1/en not_active Ceased
- 2011-12-20 AU AU2011383722A patent/AU2011383722B2/en not_active Ceased
- 2011-12-20 SG SG11201402848YA patent/SG11201402848YA/en unknown
- 2011-12-20 RU RU2014129826A patent/RU2014129826A/ru unknown
- 2011-12-20 MX MX2014007555A patent/MX2014007555A/es not_active Application Discontinuation
- 2011-12-20 JP JP2014548743A patent/JP2015500874A/ja active Pending
- 2011-12-20 CN CN201180075710.5A patent/CN103987684A/zh active Pending
- 2011-12-20 CA CA2858954A patent/CA2858954A1/en not_active Abandoned
- 2011-12-20 EP EP11810737.4A patent/EP2794534B1/en not_active Not-in-force
-
2012
- 2012-12-18 AR ARP120104803A patent/AR089310A1/es unknown
- 2012-12-19 TW TW101148200A patent/TWI504585B/zh not_active IP Right Cessation
-
2014
- 2014-06-10 ZA ZA2014/04277A patent/ZA201404277B/en unknown
- 2014-06-17 PH PH12014501367A patent/PH12014501367A1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JP2015500874A (ja) | 2015-01-08 |
| WO2013095361A1 (en) | 2013-06-27 |
| SG11201402848YA (en) | 2014-10-30 |
| RU2014129826A (ru) | 2016-02-10 |
| CA2858954A1 (en) | 2013-06-27 |
| AU2011383722A1 (en) | 2014-06-19 |
| ZA201404277B (en) | 2016-05-25 |
| EP2794534B1 (en) | 2016-11-30 |
| US20140357902A1 (en) | 2014-12-04 |
| US9000231B2 (en) | 2015-04-07 |
| BR112014014255A2 (pt) | 2017-06-13 |
| AU2011383722B2 (en) | 2015-03-12 |
| MX2014007555A (es) | 2014-08-01 |
| TW201339129A (zh) | 2013-10-01 |
| TWI504585B (zh) | 2015-10-21 |
| EP2794534A1 (en) | 2014-10-29 |
| CN103987684A (zh) | 2014-08-13 |
| PH12014501367A1 (en) | 2014-09-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FB | Suspension of granting procedure |