AR008526A1 - PROCEDURE FOR PREPARING BENZYL ETHERS. - Google Patents
PROCEDURE FOR PREPARING BENZYL ETHERS.Info
- Publication number
- AR008526A1 AR008526A1 ARP970105381A ARP970105381A AR008526A1 AR 008526 A1 AR008526 A1 AR 008526A1 AR P970105381 A ARP970105381 A AR P970105381A AR P970105381 A ARP970105381 A AR P970105381A AR 008526 A1 AR008526 A1 AR 008526A1
- Authority
- AR
- Argentina
- Prior art keywords
- 4alkyl
- reaction
- general formula
- halogen
- 6alkyl
- Prior art date
Links
- -1 BENZYL ETHERS Chemical class 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 3
- 229910052736 halogen Inorganic materials 0.000 abstract 3
- 150000002367 halogens Chemical class 0.000 abstract 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 150000002170 ethers Chemical class 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 abstract 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 abstract 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- 125000002723 alicyclic group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 239000003963 antioxidant agent Substances 0.000 abstract 1
- 230000003078 antioxidant effect Effects 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 238000011031 large-scale manufacturing process Methods 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 239000003444 phase transfer catalyst Substances 0.000 abstract 1
- 238000007086 side reaction Methods 0.000 abstract 1
Classifications
-
- 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
- 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
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/54—Radicals substituted by oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Un procedimiento para preparar éteres mixtos de formula general (I), en donde Ar representa un resto alicíclico, aromático o un resto hetero-cíclicocon uno o más heteroátomos, que se encuentra eventualmente sustituido con uno o más grupos de alcoxi C1-4, metilendioxi, alquilo C1-4, halogeno,haloalquilo C1-4 o nitro y/o se encuentra condensado con un anillo bencénico; R1 representa hidrogeno, alquilo C1-4, haloalquilo C1-4, alquenilo C2-4,fenilo, fenilo sustituido o cicloalquilo C3-6; R2representa alquilo C1-6, alquenilo C3-6 o alquinilo C3-6 eventualmente mono- o polisustituido con ungrupo de alquilo C1-6, alcoxi (C1-6), alquenilo C3-6, alquinilo C3-6, haloalquilo C1-6 o un átomo de halogeno; o representa un grupo dealquil (C1-4)oxi-alquil (C1-4) oxi-alquilo (C1-4); n es 1, 2, por reaccion de compuestos de formula general (II), en donde R1 y n tienen el significado indicado másarriba, X representa hidroxi, halogeno o un grupo saliente de éster sulfonico, con compuestos de formula general (III), R2 - Y en donde R2 tiene el mismosignificado que el indicado más arriba e Y representa hidroxi, halogeno o un grupo saliente de éster sulfonico, con la condicion de que uno de losparticipantes de la reaccionde formulas generales (II) y (III) sea un alcohol, caracterizado porque la reaccion se lleva a cabo en condicionesheterogéneas y en presencia de una base acuosa y de un catalizador de transferencia de fase, y el producto resultante se estabiliza eventualmentepor adicion de una base y/o de un antioxidante. El procedimiento del invento permite preparar los éteres de formula general (I) evitando el empleo dereactivos caros y las posibles reacciones secundarias, y asegurando una produccion a gran escala sin riesgos debido a que la reaccion puede ser llevadaA process for preparing mixed ethers of general formula (I), in which Ar represents an alicyclic, aromatic or heterocyclic moiety with one or more heteroatoms, which is optionally substituted with one or more C1-4 alkoxy groups, methylenedioxy , C1-4alkyl, halogen, C1-4alkyl or nitro and / or is condensed with a benzene ring; R1 represents hydrogen, C1-4 alkyl, C1-4 haloalkyl, C2-4 alkenyl, phenyl, substituted phenyl or C3-6 cycloalkyl; R2 represents C1-6alkyl, C3-6alkenyl or C3-6alkynyl, optionally mono- or polysubstituted with a group of C1-6alkyl, (C1-6) alkoxy, C3-6alkynyl, C1-6alkyl or a halogen atom; or represents a (1-4C) alkyl oxy-C1-4alkyl oxy-C1-4alkyl group; n is 1, 2, by reaction of compounds of general formula (II), where R1 and n have the meaning indicated above, X represents hydroxy, halogen or a leaving group of sulfonic ester, with compounds of general formula (III), R2 - Y where R2 has the same meaning as the one indicated above and Y represents hydroxy, halogen or a leaving group of sulfonic ester, with the proviso that one of the participants in the reaction of general formulas (II) and (III) is an alcohol characterized in that the reaction is carried out under heterogeneous conditions and in the presence of an aqueous base and a phase transfer catalyst, and the resulting product is eventually stabilized by the addition of a base and / or an antioxidant. The process of the invention allows the ethers of general formula (I) to be prepared avoiding the use of expensive reagents and possible side reactions, and ensuring a large-scale production without risks because the reaction can be carried out
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU9603178A HU220961B1 (en) | 1996-11-18 | 1996-11-18 | Process for producing benzyl-ethers with phase transformation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR008526A1 true AR008526A1 (en) | 2000-01-19 |
Family
ID=89994453
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP970105381A AR008526A1 (en) | 1996-11-18 | 1997-11-18 | PROCEDURE FOR PREPARING BENZYL ETHERS. |
Country Status (7)
| Country | Link |
|---|---|
| AR (1) | AR008526A1 (en) |
| AU (1) | AU5064498A (en) |
| HR (1) | HRP970607A2 (en) |
| HU (1) | HU220961B1 (en) |
| TW (1) | TW434214B (en) |
| WO (1) | WO1998022417A1 (en) |
| ZA (1) | ZA9710317B (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6596870B2 (en) | 2000-07-13 | 2003-07-22 | Brandeis University | Asymmetric synthetic methods based on phase transfer catalysis |
| CN1124246C (en) * | 2000-09-01 | 2003-10-15 | 中国科学院上海有机化学研究所 | Process for preparing 4-(2-alkoxyethyl) phenol by phase-transfer catalysis |
| EP2289889A1 (en) | 2009-08-18 | 2011-03-02 | Endura S.p.a. | Substituted alkynyl phenoxy compounds and their uses |
| GB201104156D0 (en) * | 2011-03-11 | 2011-04-27 | Rothamstead Res Ltd | Compositions and methods for controlling pesticide resistant pests |
| GB2512112B (en) * | 2013-03-21 | 2016-03-30 | Rothamsted Res Ltd | Compositions and methods for controlling herbicide resistant weeds |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4433179A (en) * | 1980-08-25 | 1984-02-21 | Ciba-Geigy Corporation | Process for the preparation of di- and poly-allyl ethers |
| GB2198725B (en) * | 1986-11-05 | 1991-01-16 | Alter Sa | Use of a series of quaternary ammonium salts as phase-transfer catalysts |
-
1996
- 1996-11-18 HU HU9603178A patent/HU220961B1/en not_active IP Right Cessation
-
1997
- 1997-11-12 AU AU50644/98A patent/AU5064498A/en not_active Abandoned
- 1997-11-12 WO PCT/HU1997/000074 patent/WO1998022417A1/en active Application Filing
- 1997-11-13 HR HRP9603178A patent/HRP970607A2/en not_active Application Discontinuation
- 1997-11-14 ZA ZA9710317A patent/ZA9710317B/en unknown
- 1997-11-18 AR ARP970105381A patent/AR008526A1/en unknown
- 1997-12-27 TW TW086119822A patent/TW434214B/en active
Also Published As
| Publication number | Publication date |
|---|---|
| HUP9603178A2 (en) | 1998-09-28 |
| HRP970607A2 (en) | 1998-08-31 |
| HUP9603178A3 (en) | 1999-05-28 |
| HU9603178D0 (en) | 1997-01-28 |
| AU5064498A (en) | 1998-06-10 |
| HU220961B1 (en) | 2002-07-29 |
| TW434214B (en) | 2001-05-16 |
| ZA9710317B (en) | 1998-06-10 |
| WO1998022417A1 (en) | 1998-05-28 |
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