HUP0302818A2 - Eljárás 2,2-dimetil-5-(4-klór-benzil)-ciklopentanon és egy intermediere előállítására - Google Patents
Eljárás 2,2-dimetil-5-(4-klór-benzil)-ciklopentanon és egy intermediere előállításáraInfo
- Publication number
- HUP0302818A2 HUP0302818A2 HU0302818A HUP0302818A HUP0302818A2 HU P0302818 A2 HUP0302818 A2 HU P0302818A2 HU 0302818 A HU0302818 A HU 0302818A HU P0302818 A HUP0302818 A HU P0302818A HU P0302818 A2 HUP0302818 A2 HU P0302818A2
- Authority
- HU
- Hungary
- Prior art keywords
- chlorobenzyl
- dimethyl
- dimethylcyclopentanone
- cyano
- cyclopentanone
- Prior art date
Links
- DLPBZANLIRTMKU-UHFFFAOYSA-N 5-[(4-chlorophenyl)methyl]-2,2-dimethylcyclopentan-1-one Chemical compound O=C1C(C)(C)CCC1CC1=CC=C(Cl)C=C1 DLPBZANLIRTMKU-UHFFFAOYSA-N 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 2
- WIZODEKGBHNUQS-UHFFFAOYSA-N 1-[(4-chlorophenyl)methyl]-3,3-dimethyl-2-oxocyclopentane-1-carbonitrile Chemical compound O=C1C(C)(C)CCC1(C#N)CC1=CC=C(Cl)C=C1 WIZODEKGBHNUQS-UHFFFAOYSA-N 0.000 abstract 2
- GBRNFMUKXFZFRJ-UHFFFAOYSA-N 2,2-dimethylhexanedinitrile Chemical compound N#CC(C)(C)CCCC#N GBRNFMUKXFZFRJ-UHFFFAOYSA-N 0.000 abstract 2
- KHIAKCIMIJQSIO-UHFFFAOYSA-N 2-amino-3,3-dimethylcyclopentene-1-carbonitrile Chemical compound CC1(C)CCC(C#N)=C1N KHIAKCIMIJQSIO-UHFFFAOYSA-N 0.000 abstract 2
- AEQAVKREMWDWAE-UHFFFAOYSA-N 3,3-dimethyl-2-oxocyclopentane-1-carbonitrile Chemical compound CC1(C)CCC(C#N)C1=O AEQAVKREMWDWAE-UHFFFAOYSA-N 0.000 abstract 2
- AGJFOWMZIAASOW-UHFFFAOYSA-N 5-chloro-2,2-dimethylpentanenitrile Chemical compound N#CC(C)(C)CCCCl AGJFOWMZIAASOW-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 239000012454 non-polar solvent Substances 0.000 abstract 2
- JQZAEUFPPSRDOP-UHFFFAOYSA-N 1-chloro-4-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C=C1 JQZAEUFPPSRDOP-UHFFFAOYSA-N 0.000 abstract 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 abstract 1
- MFESCIUQSIBMSM-UHFFFAOYSA-N I-BCP Chemical compound ClCCCBr MFESCIUQSIBMSM-UHFFFAOYSA-N 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- LRDFRRGEGBBSRN-UHFFFAOYSA-N isobutyronitrile Chemical compound CC(C)C#N LRDFRRGEGBBSRN-UHFFFAOYSA-N 0.000 abstract 1
- 239000003444 phase transfer catalyst Substances 0.000 abstract 1
- 239000003880 polar aprotic solvent Substances 0.000 abstract 1
- 238000007363 ring formation reaction Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/45—Carboxylic acid nitriles having cyano groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C255/46—Carboxylic acid nitriles having cyano groups bound to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of non-condensed rings
-
- 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/687—Unsaturated compounds containing a keto groups being part of a ring containing halogen
- C07C49/697—Unsaturated compounds containing a keto groups being part of a ring containing halogen containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
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
A találmány tárgya eljárás az képletű 2,2-dimetil-5-(4-klór-benzil)-ciklopentanon előállítására úgy hogy (a) izobutironitrilt 1-bróm-3-klór-propánnal reagáltatnak egy első bázis jelenlétében nempolárisoldószerben 5-klór-2,2-dimetil-pentánnitrillé; (b) az 5-klór-2,2-dimetil-pentánnitrilt cianidforrás reagenssel fázistranszferkatalizátor jelenlétében 2,2-dimetil-adiponitrillé reagáltatják; (c) a2,2-dimetil-adiponitril egy második bázis jelenlétében nempolárisoldószerben 3,3-dimetil-2-amino-l-ciano-ciklopenténné ciklizálják; (d)a 3,3-dimetil-2-amino-l-ciano-ciklopentént egy sav jelelétében 5-ciano-2,2-dimetil-ciklopentanonná hidrolizálják; (e) az 5-ciano-2,2-dimetil-ciklopentanont 4-klór-benzil-kloriddal egy harmadik bázisjelenlétében poláris aprotikus oldószerben 5-(4-klór-benzil)-5-ciano-2,2-dimetil-ciklopentanonná reagáltatják; és (f) az 5-(4-klór-benzil)-5-ciano-2,2-dimetil-ciklopentanont végül egy sav jelenlétében a kívánt5-(4-klór-benzil)-2,2-dimetil-ciklopentanonná hidrolizálják. Ó
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US21076800P | 2000-06-12 | 2000-06-12 | |
PCT/EP2001/006578 WO2002000608A2 (en) | 2000-06-12 | 2001-06-11 | A process for the preparation of 2,2-dimethyl-5-(4-chlorobenzyl) cyclopentanone and an intermediate useful therefor |
Publications (2)
Publication Number | Publication Date |
---|---|
HUP0302818A2 true HUP0302818A2 (hu) | 2004-01-28 |
HUP0302818A3 HUP0302818A3 (en) | 2005-01-28 |
Family
ID=22784187
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HU0302818A HUP0302818A3 (en) | 2000-06-12 | 2001-06-11 | A process for the preparation of 2,2-dimethyl-5-(4-chlorobenzyl)cyclopentanone and an intermediate useful therefor |
Country Status (13)
Country | Link |
---|---|
US (1) | US6344580B1 (hu) |
EP (1) | EP1289938B1 (hu) |
JP (1) | JP2004501894A (hu) |
KR (1) | KR20030029055A (hu) |
AT (1) | ATE266629T1 (hu) |
AU (1) | AU2001275678A1 (hu) |
BR (1) | BR0111586A (hu) |
DE (1) | DE60103274T2 (hu) |
DK (1) | DK1289938T3 (hu) |
ES (1) | ES2220785T3 (hu) |
HU (1) | HUP0302818A3 (hu) |
IL (1) | IL152836A0 (hu) |
WO (1) | WO2002000608A2 (hu) |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7166750B1 (en) * | 2000-08-11 | 2007-01-23 | Kureha Corporation | Process for the preparation of 5-[(4-chlorophenyl)methyl]-2,2-dimethylcyclopentanone |
AU2003293308A1 (en) | 2003-09-17 | 2005-04-27 | Carl Zeiss Smt Ag | Masks, lithography device and semiconductor component |
WO2005058860A1 (ja) * | 2003-12-19 | 2005-06-30 | Ube Industries, Ltd. | 4−置換又は非置換テトラヒドロピラン−4−カルボン酸化合物又はそのエステル化合物の製法 |
CN102204546B (zh) * | 2011-04-16 | 2014-02-05 | 陕西汤普森生物科技有限公司 | 一种含噻呋酰胺与三唑类化合物的杀菌组合物 |
JP5858998B2 (ja) * | 2011-06-07 | 2016-02-10 | 株式会社クレハ | シクロペンタノン化合物の製造方法、および中間体化合物 |
EP2719693B1 (en) | 2011-06-07 | 2016-08-10 | Kureha Corporation | Method for manufacturing oxetane compound, method for manufacturing azolylmethylcyclopentanol compound, and intermediate compound |
CN107365262B (zh) * | 2016-05-11 | 2019-10-29 | 杭州宇龙化工有限公司 | 一种5,5-二甲基-2-氰基环戊酮的制备方法 |
CN114773279B (zh) * | 2022-04-13 | 2023-12-05 | 浙江工业大学 | 一种叶菌唑的新合成方法 |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5239089A (en) * | 1986-11-10 | 1993-08-24 | Kureha Kagaku Kogyo Kabushiki Kaisha | Oxirane derivatives useful for making fungicidal azole compounds |
JPH0625140B2 (ja) | 1986-11-10 | 1994-04-06 | 呉羽化学工業株式会社 | 新規アゾール誘導体、その製造方法及び該誘導体の農園芸用薬剤 |
JPH07138234A (ja) * | 1993-11-11 | 1995-05-30 | Kureha Chem Ind Co Ltd | アゾリルメチルシクロアルカノール誘導体の製造方法 |
JPH08245517A (ja) | 1995-03-10 | 1996-09-24 | Kureha Chem Ind Co Ltd | アルキルシクロペンタノン誘導体の製造方法 |
-
2001
- 2001-06-08 US US09/878,000 patent/US6344580B1/en not_active Expired - Fee Related
- 2001-06-11 AU AU2001275678A patent/AU2001275678A1/en not_active Abandoned
- 2001-06-11 IL IL15283601A patent/IL152836A0/xx unknown
- 2001-06-11 DE DE60103274T patent/DE60103274T2/de not_active Expired - Lifetime
- 2001-06-11 ES ES01953167T patent/ES2220785T3/es not_active Expired - Lifetime
- 2001-06-11 WO PCT/EP2001/006578 patent/WO2002000608A2/en active IP Right Grant
- 2001-06-11 JP JP2002505356A patent/JP2004501894A/ja not_active Withdrawn
- 2001-06-11 DK DK01953167T patent/DK1289938T3/da active
- 2001-06-11 AT AT01953167T patent/ATE266629T1/de not_active IP Right Cessation
- 2001-06-11 HU HU0302818A patent/HUP0302818A3/hu unknown
- 2001-06-11 BR BR0111586-3A patent/BR0111586A/pt not_active IP Right Cessation
- 2001-06-11 KR KR1020027016855A patent/KR20030029055A/ko not_active Application Discontinuation
- 2001-06-11 EP EP01953167A patent/EP1289938B1/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
ES2220785T3 (es) | 2004-12-16 |
JP2004501894A (ja) | 2004-01-22 |
HUP0302818A3 (en) | 2005-01-28 |
AU2001275678A1 (en) | 2002-01-08 |
EP1289938A2 (en) | 2003-03-12 |
DE60103274D1 (de) | 2004-06-17 |
WO2002000608A3 (en) | 2002-05-30 |
ATE266629T1 (de) | 2004-05-15 |
WO2002000608A2 (en) | 2002-01-03 |
DE60103274T2 (de) | 2004-09-02 |
US6344580B1 (en) | 2002-02-05 |
BR0111586A (pt) | 2003-05-06 |
DK1289938T3 (da) | 2004-06-28 |
IL152836A0 (en) | 2003-06-24 |
US20020013489A1 (en) | 2002-01-31 |
KR20030029055A (ko) | 2003-04-11 |
EP1289938B1 (en) | 2004-05-12 |
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