MX170385B - Proceso para la produccion de compuestos disetonicos acilados - Google Patents
Proceso para la produccion de compuestos disetonicos aciladosInfo
- Publication number
- MX170385B MX170385B MX001041A MX104185A MX170385B MX 170385 B MX170385 B MX 170385B MX 001041 A MX001041 A MX 001041A MX 104185 A MX104185 A MX 104185A MX 170385 B MX170385 B MX 170385B
- Authority
- MX
- Mexico
- Prior art keywords
- cyanide
- cyanohydrin
- rearrangement
- enol ester
- conducted
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title 1
- -1 acylated cyclic diketone compound Chemical class 0.000 abstract 8
- 230000008707 rearrangement Effects 0.000 abstract 3
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 abstract 2
- 230000003197 catalytic effect Effects 0.000 abstract 2
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 abstract 2
- ZDBRPNZOTCHLSP-UHFFFAOYSA-N 1-hydroxycyclohexane-1-carbonitrile Chemical compound N#CC1(O)CCCCC1 ZDBRPNZOTCHLSP-UHFFFAOYSA-N 0.000 abstract 1
- ZRXHLJNBNWVNIM-UHFFFAOYSA-N 3-methyl-1-benzofuran Chemical compound C1=CC=C2C(C)=COC2=C1 ZRXHLJNBNWVNIM-UHFFFAOYSA-N 0.000 abstract 1
- 125000002015 acyclic group Chemical group 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000005103 alkyl silyl group Chemical group 0.000 abstract 1
- 239000002585 base Substances 0.000 abstract 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- HJSLFCCWAKVHIW-UHFFFAOYSA-N cyclohexane-1,3-dione Chemical compound O=C1CCCC(=O)C1 HJSLFCCWAKVHIW-UHFFFAOYSA-N 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- WOFDVDFSGLBFAC-UHFFFAOYSA-N lactonitrile Chemical compound CC(O)C#N WOFDVDFSGLBFAC-UHFFFAOYSA-N 0.000 abstract 1
- NNICRUQPODTGRU-UHFFFAOYSA-N mandelonitrile Chemical compound N#CC(O)C1=CC=CC=C1 NNICRUQPODTGRU-UHFFFAOYSA-N 0.000 abstract 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
- C07C319/20—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by reactions not involving the formation of sulfide groups
-
- 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
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/455—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation with carboxylic acids or their derivatives
-
- 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
- C07C45/54—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 of compounds containing doubly bound oxygen atoms, e.g. esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/385—Saturated compounds containing a keto group being part of a ring
- C07C49/403—Saturated compounds containing a keto group being part of a ring of a six-membered ring
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)
- Catalysts (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
La presente invención se refiere a un proceso para producir un compuesto dicetónico cíclico acilado siendo este substancialmente un derivado benzoilo substituído de una 1,3-ciclohexanodiona, caracterizado por la redisposición del enol ester correspondiente, en el cual se conduce la redisposición en la presencia de una fuente de cianuro, la cual es un cianuro alcalino metálico, una cianohidrina de una cetona alquilometílica que tiene de 1 a 4 átomos de carbono en el grupo alquilo, cianohidrina de benzaldehido, cianohidrina de ciclohexanona, una cianohidrina de un aldehido alifático con C2-C5, lactonitrilo, un cianuro silil alquilo inferior, ferricianuro de potasio o cianuro de hidrógeno, en donde tal redisposición es conducida a temperaturas de hasta 80 grados C en la presencia de ya sea (a) una cantidad catalítica de una fuente de cianuro y u n exceso molar, con respecto al enol ester, de una base moderada; o b) una cantidad estequiometrica, con respecto al enol ester, de cianuro de potasio o cianuro de litio y una cantidad catalítica de un ester cíclico Crown o un análogo acíclico del mismo.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US68388284A | 1984-12-20 | 1984-12-20 | |
| US79884285A | 1985-11-20 | 1985-11-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MX170385B true MX170385B (es) | 1993-08-19 |
Family
ID=27103213
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MX001041A MX170385B (es) | 1984-12-20 | 1985-12-20 | Proceso para la produccion de compuestos disetonicos acilados |
Country Status (24)
| Country | Link |
|---|---|
| EP (1) | EP0186117B1 (es) |
| JP (1) | JPH0710787B2 (es) |
| KR (1) | KR920000907B1 (es) |
| CN (1) | CN1003588B (es) |
| AU (1) | AU592069B2 (es) |
| BG (1) | BG45042A3 (es) |
| BR (1) | BR8506421A (es) |
| CA (1) | CA1317976C (es) |
| DE (1) | DE3580657D1 (es) |
| DK (1) | DK174911B1 (es) |
| FI (1) | FI86542C (es) |
| GE (1) | GEP19960642B (es) |
| GR (1) | GR853110B (es) |
| HU (1) | HU204753B (es) |
| IL (1) | IL77350A (es) |
| MX (1) | MX170385B (es) |
| NO (1) | NO163402C (es) |
| PL (1) | PL148102B1 (es) |
| PT (1) | PT81730B (es) |
| RO (1) | RO93561A (es) |
| SU (1) | SU1697591A3 (es) |
| TR (1) | TR23030A (es) |
| YU (1) | YU45754B (es) |
| ZW (1) | ZW23785A1 (es) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL77349A (en) * | 1984-12-20 | 1990-07-12 | Stauffer Chemical Co | 2-(2'-nitrobenzoyl)-1,3-cyclohexanediones,their preparation and their use as herbicides |
| IL77348A (en) * | 1984-12-20 | 1991-05-12 | Stauffer Chemical Co | 2-(2'-substituted benzoyl)-1,3-cyclohexanediones,their preparation and their use as herbicides |
| TR22585A (tr) * | 1984-12-20 | 1987-12-07 | Stauffer Chemical Co | Bazi 2-(2'-alkilbenzoil)-1,3-sikloheksandion'lar |
| AU583089B2 (en) * | 1985-02-15 | 1989-04-20 | Ici Australia Limited | Process for the preparation of 2-acylcyclohexane-1,3-dione derivatives |
| US4724263A (en) * | 1986-06-09 | 1988-02-09 | Stauffer Chemical Company | Certain 2-phenylacetyl-1,3,5-cyclohexanetriones |
| US4783213A (en) * | 1986-10-16 | 1988-11-08 | Stauffer Chemical Company | Certain 2-(2-substituted benzoyl)-4-(substituted oxy or substituted thio)-1,3-cyclohexanediones |
| US4808214A (en) * | 1986-10-16 | 1989-02-28 | Stauffer Chemical Company | Certain 2-(2-substituted benzoyl)-4-(substituted oxy or substituted thio)-1,3-cyclohexanediones |
| KR890003680A (ko) * | 1986-10-16 | 1989-04-17 | 죤 알.페넬 | 2-(2-치환 벤조일)-4-(치환)-1,3-시클로헥산디온 및 그 제조방법과 이를 이용한 조성물 및 식물체의 억제방법 |
| DE3743695A1 (de) * | 1987-12-18 | 1989-06-29 | Schering Ag | 4-benzoyl-3-hydroxy-5-oxo-3-cyclohexencarbonsaeurederivate, verfahren zur herstellung dieser verbindungen und ihre verwendung als mittel mit pflanzenwachstumsregulierender wirkung |
| HUT50312A (en) * | 1988-02-01 | 1990-01-29 | Sandoz Ag | Herbicide composition containing new dion-compounds and process for producing these compounds |
| DK184489A (da) * | 1988-04-18 | 1989-10-19 | Sandoz Ag | Bicyclodioner |
| US4869748A (en) * | 1988-12-02 | 1989-09-26 | Ici Americas Inc. | Certain 3-(substituted benzoyl)-3:2:1-bicyclooctan-2,4-diones |
| US5336662A (en) * | 1989-04-25 | 1994-08-09 | Sandoz Ltd. | Heterocyclic diones as plant growth regulators |
| KR927003554A (ko) * | 1990-10-25 | 1992-12-18 | 예안 크레이머 | 살충제 및 식물 생장 조절제로서의 헤테로 사이클계 디온 유도체 |
| GB9501433D0 (en) * | 1995-01-25 | 1995-03-15 | Zeneca Ltd | Chemical process |
| GB9501434D0 (en) * | 1995-01-25 | 1995-03-15 | Zeneca Ltd | Chemical process |
| DE10113137C2 (de) * | 2001-03-17 | 2003-05-15 | Bayer Cropscience Gmbh | Verfahren zur Herstellung von substituierten 2-Benzoyl-1,3-cyclohexandionen |
| AU2003203482B2 (en) * | 2002-04-09 | 2005-06-02 | Syngenta Participations Ag | Process for the preparation of cyclic diketones |
| TWI348999B (en) * | 2003-10-02 | 2011-09-21 | Syngenta Participations Ag | Process |
| DE102004016496A1 (de) | 2004-04-03 | 2005-10-20 | Bayer Cropscience Gmbh | Herbizid wirksame 3-Amino-2-thiomethyl-benzoylpyrazole |
| DE102007026875A1 (de) | 2007-06-11 | 2008-12-24 | Bayer Cropscience Ag | 3-Cyclopropyl-4-(3-thiobenzoyl)pyrazole und ihre Verwendung als Herbizide |
| PT104664A (pt) * | 2009-07-07 | 2011-01-07 | Sapec Agro S A | Polimorfo cristalino estável de 2-(2-cloro-4-mesil-benzoil)- ciclo-hexano-1,3-diona e processo para preparar o mesmo |
| CN102781235B (zh) | 2010-02-19 | 2015-04-22 | 拜耳知识产权有限责任公司 | 3-氨基羰基-取代的苯甲酰环己二酮和它们作为除草剂的用途 |
| JP5883860B2 (ja) | 2010-07-21 | 2016-03-15 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ ＧｍｂＨ | ４−（４−ハロゲンアルキル−３−チオベンゾイル）ピラゾール類及び除草剤としてのそれらの使用 |
| US9084425B2 (en) | 2011-07-15 | 2015-07-21 | Bayer Intellectual Property Gmbh | 2,3-diphenyl-valeronitrile derivatives, method for the production thereof and use thereof as herbicides and plant growth regulators |
| CN113845451B (zh) * | 2020-06-28 | 2023-07-14 | 沈阳中化农药化工研发有限公司 | 一种制备三酮类除草剂的方法 |
| CN113233998B (zh) * | 2021-05-24 | 2021-12-28 | 浙江新安化工集团股份有限公司 | 一种硝磺草酮的制备方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4350705A (en) * | 1979-03-31 | 1982-09-21 | Eisai Co., Ltd. | Cyclohexane derivatives, process for preparation thereof and medicines containing these cyclohexane derivatives |
| EP0090262B1 (en) * | 1982-03-25 | 1992-08-05 | Stauffer Chemical Company | Certain 2-(2-substituted benzoyl)-1,3-cyclohexanediones |
| JPS59196840A (ja) * | 1983-04-22 | 1984-11-08 | Kumiai Chem Ind Co Ltd | シクロヘキサン誘導体および植物生長調節剤 |
| US4482727A (en) * | 1983-07-01 | 1984-11-13 | Stauffer Chemical Company | Certain 1,3-cyclohexanedione adducts of substituted phenoxyphenoxypropionic acids and their use as an herbicide |
| DE3568975D1 (en) * | 1984-05-21 | 1989-04-27 | Stauffer Chemical Co | Certain 2-(2-(substituted phenyl)acetyl)-1,3-cyclohexanediones |
| IL77349A (en) * | 1984-12-20 | 1990-07-12 | Stauffer Chemical Co | 2-(2'-nitrobenzoyl)-1,3-cyclohexanediones,their preparation and their use as herbicides |
| TR22585A (tr) * | 1984-12-20 | 1987-12-07 | Stauffer Chemical Co | Bazi 2-(2'-alkilbenzoil)-1,3-sikloheksandion'lar |
-
1985
- 1985-12-16 IL IL77350A patent/IL77350A/xx not_active IP Right Cessation
- 1985-12-17 AU AU51335/85A patent/AU592069B2/en not_active Expired
- 1985-12-17 KR KR1019850009490A patent/KR920000907B1/ko not_active Expired
- 1985-12-18 DE DE8585116161T patent/DE3580657D1/de not_active Expired - Lifetime
- 1985-12-18 EP EP85116161A patent/EP0186117B1/en not_active Expired - Lifetime
- 1985-12-18 FI FI855047A patent/FI86542C/fi not_active IP Right Cessation
- 1985-12-19 DK DK198505945A patent/DK174911B1/da not_active IP Right Cessation
- 1985-12-19 HU HU854874A patent/HU204753B/hu unknown
- 1985-12-19 ZW ZW237/85A patent/ZW23785A1/xx unknown
- 1985-12-19 CN CN85109777.4A patent/CN1003588B/zh not_active Expired
- 1985-12-19 SU SU853995138A patent/SU1697591A3/ru active
- 1985-12-19 PT PT81730A patent/PT81730B/pt unknown
- 1985-12-19 NO NO855163A patent/NO163402C/no not_active IP Right Cessation
- 1985-12-19 CA CA000498209A patent/CA1317976C/en not_active Expired - Lifetime
- 1985-12-20 GR GR853110A patent/GR853110B/el not_active IP Right Cessation
- 1985-12-20 PL PL1985256982A patent/PL148102B1/pl unknown
- 1985-12-20 TR TR51032/85A patent/TR23030A/xx unknown
- 1985-12-20 JP JP28758885A patent/JPH0710787B2/ja not_active Expired - Lifetime
- 1985-12-20 MX MX001041A patent/MX170385B/es unknown
- 1985-12-20 BR BR8506421A patent/BR8506421A/pt not_active IP Right Cessation
- 1985-12-20 RO RO85121246A patent/RO93561A/ro unknown
- 1985-12-20 YU YU200985A patent/YU45754B/sh unknown
- 1985-12-20 BG BG072811A patent/BG45042A3/xx unknown
-
1994
- 1994-10-07 GE GEAP19942241A patent/GEP19960642B/en unknown
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