UA73364C2 - Спосіб одержання 5-[(4-хлорфеніл)метил]-2,2-диметилциклопентанону та спосіб одержання проміжних сполук (варіанти) - Google Patents
Спосіб одержання 5-[(4-хлорфеніл)метил]-2,2-диметилциклопентанону та спосіб одержання проміжних сполук (варіанти) Download PDFInfo
- Publication number
- UA73364C2 UA73364C2 UA2003021098A UA2003021098A UA73364C2 UA 73364 C2 UA73364 C2 UA 73364C2 UA 2003021098 A UA2003021098 A UA 2003021098A UA 2003021098 A UA2003021098 A UA 2003021098A UA 73364 C2 UA73364 C2 UA 73364C2
- Authority
- UA
- Ukraine
- Prior art keywords
- methyl
- chlorophenyl
- reaction
- oxocyclopentanecarboxylic acid
- stage
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract description 22
- 238000002360 preparation method Methods 0.000 title abstract description 10
- 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
- 150000001875 compounds Chemical class 0.000 title description 10
- -1 methyl halide Chemical class 0.000 abstract description 51
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 17
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 abstract description 10
- 239000012312 sodium hydride Substances 0.000 abstract description 10
- 229910000104 sodium hydride Inorganic materials 0.000 abstract description 10
- 230000007062 hydrolysis Effects 0.000 abstract description 9
- 238000006460 hydrolysis reaction Methods 0.000 abstract description 9
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 abstract description 7
- 239000000417 fungicide Substances 0.000 abstract description 6
- 239000005868 Metconazole Substances 0.000 abstract description 5
- XWPZUHJBOLQNMN-UHFFFAOYSA-N metconazole Chemical compound C1=NC=NN1CC1(O)C(C)(C)CCC1CC1=CC=C(Cl)C=C1 XWPZUHJBOLQNMN-UHFFFAOYSA-N 0.000 abstract description 5
- 230000000855 fungicidal effect Effects 0.000 abstract description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- HHMMBIXXONUWEH-UHFFFAOYSA-N ethyl 1-[(4-chlorophenyl)methyl]-3-methyl-2-oxocyclopentane-1-carboxylate Chemical compound C=1C=C(Cl)C=CC=1CC1(C(=O)OCC)CCC(C)C1=O HHMMBIXXONUWEH-UHFFFAOYSA-N 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- DCLNQHDBQDTZAT-UHFFFAOYSA-N methyl 1-[(4-chlorophenyl)methyl]-3-methyl-2-oxocyclopentane-1-carboxylate Chemical compound C=1C=C(Cl)C=CC=1CC1(C(=O)OC)CCC(C)C1=O DCLNQHDBQDTZAT-UHFFFAOYSA-N 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 55
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
- 239000002904 solvent Substances 0.000 description 28
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 23
- 150000004702 methyl esters Chemical class 0.000 description 22
- 229910052751 metal Inorganic materials 0.000 description 20
- 239000002184 metal Substances 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 14
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 13
- UDSFAEKRVUSQDD-UHFFFAOYSA-N Dimethyl adipate Chemical compound COC(=O)CCCCC(=O)OC UDSFAEKRVUSQDD-UHFFFAOYSA-N 0.000 description 12
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 12
- 239000007795 chemical reaction product Substances 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 11
- JQZAEUFPPSRDOP-UHFFFAOYSA-N 1-chloro-4-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C=C1 JQZAEUFPPSRDOP-UHFFFAOYSA-N 0.000 description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
- 238000004821 distillation Methods 0.000 description 10
- 159000000000 sodium salts Chemical class 0.000 description 10
- 230000003993 interaction Effects 0.000 description 9
- 239000000047 product Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 229940102396 methyl bromide Drugs 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- FXBPINRBSNMESY-UHFFFAOYSA-N 2-oxocyclopentane-1-carboxylic acid Chemical compound OC(=O)C1CCCC1=O FXBPINRBSNMESY-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
- 206010062717 Increased upper airway secretion Diseases 0.000 description 5
- 150000004703 alkoxides Chemical class 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000006114 decarboxylation reaction Methods 0.000 description 5
- 208000026435 phlegm Diseases 0.000 description 5
- CILHIWHGZQDNQJ-UHFFFAOYSA-N 1-methyl-2-oxocyclopentane-1-carboxylic acid Chemical compound OC(=O)C1(C)CCCC1=O CILHIWHGZQDNQJ-UHFFFAOYSA-N 0.000 description 4
- DPBQIRNFTKVJPK-UHFFFAOYSA-N 3-methyl-2-oxocyclopentane-1-carboxylic acid Chemical compound CC1CCC(C(O)=O)C1=O DPBQIRNFTKVJPK-UHFFFAOYSA-N 0.000 description 4
- VIZORQUEIQEFRT-UHFFFAOYSA-N Diethyl adipate Chemical compound CCOC(=O)CCCCC(=O)OCC VIZORQUEIQEFRT-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000004817 gas chromatography Methods 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 239000002798 polar solvent Substances 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 150000001491 aromatic compounds Chemical class 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000006482 condensation reaction Methods 0.000 description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
- 150000004704 methoxides Chemical class 0.000 description 3
- 238000007069 methylation reaction Methods 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- YWKSINPSASCIMZ-UHFFFAOYSA-N 4,5-dimethyl-4,5-dihydro-1h-imidazole Chemical compound CC1NC=NC1C YWKSINPSASCIMZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000000010 aprotic solvent Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- UOBSVARXACCLLH-UHFFFAOYSA-N monomethyl adipate Chemical compound COC(=O)CCCCC(O)=O UOBSVARXACCLLH-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000007142 ring opening reaction Methods 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 238000001577 simple distillation Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 235000009518 sodium iodide Nutrition 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- PRDNZKBCCWFTBJ-UHFFFAOYSA-N 1,3-dimethyl-2-oxocyclopentane-1-carboxylic acid Chemical compound CC1C(C(CC1)(C(=O)O)C)=O PRDNZKBCCWFTBJ-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 238000010934 O-alkylation reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000005217 methyl ethers Chemical class 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical compound [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 description 1
- 231100000989 no adverse effect Toxicity 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 239000007787 solid 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
- C07C45/61—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
- C07C45/676—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 by elimination of carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
- C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP26429299 | 1999-08-13 | ||
| PCT/JP2000/005401 WO2001012580A1 (fr) | 1999-08-13 | 2000-08-11 | Procede de preparation de 5-[(4-chlorophenyl)-methyl]-2,2-dimethylcyclopentanone |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA73364C2 true UA73364C2 (uk) | 2005-07-15 |
Family
ID=17401150
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA2003021098A UA73364C2 (uk) | 1999-08-13 | 2000-11-08 | Спосіб одержання 5-[(4-хлорфеніл)метил]-2,2-диметилциклопентанону та спосіб одержання проміжних сполук (варіанти) |
Country Status (12)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8975434B2 (en) | 2011-06-07 | 2015-03-10 | Kureha Corporation | Method for producing cyclopentanone compound, and intermediate compound |
| WO2015075981A1 (ja) * | 2013-11-22 | 2015-05-28 | 株式会社クレハ | カルボニル化合物の製造方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| JP2637824B2 (ja) * | 1989-08-15 | 1997-08-06 | 呉羽化学工業株式会社 | 新規アゾール置換シクロアルカノール誘導体、その製造法及び該誘導体の農園芸用殺菌剤 |
| JPH0784413B2 (ja) * | 1991-09-18 | 1995-09-13 | 呉羽化学工業株式会社 | ３−（無置換または置換ベンジル）−１−アルキル−２−オキソシクロペンタンカルボン酸アルキルエステル誘導体、その製造方法、殺菌剤及び中間体としての利用 |
| 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 |
-
2000
- 2000-08-09 TW TW089116041A patent/TW591012B/zh not_active IP Right Cessation
- 2000-08-11 WO PCT/JP2000/005401 patent/WO2001012580A1/ja active IP Right Grant
- 2000-08-11 PL PL362899A patent/PL203074B1/pl unknown
- 2000-08-11 PH PH12000002167A patent/PH12000002167B1/en unknown
- 2000-08-11 JP JP2001516881A patent/JP4979170B2/ja not_active Expired - Lifetime
- 2000-08-11 AU AU2000264750A patent/AU2000264750A1/en not_active Abandoned
- 2000-08-11 BR BRPI0017310-0A patent/BR0017310B1/pt not_active IP Right Cessation
- 2000-08-11 AR ARP000104172A patent/AR025233A1/es not_active Application Discontinuation
- 2000-08-11 HU HU0300723A patent/HUP0300723A3/hu unknown
- 2000-11-08 UA UA2003021098A patent/UA73364C2/uk unknown
-
2003
- 2003-01-30 IL IL154207A patent/IL154207A/en not_active IP Right Cessation
-
2005
- 2005-12-20 IN IN5932DE2005 patent/IN2005DE05932A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPWO0112580A1 (en) | 2003-03-11 |
| JP4979170B2 (ja) | 2012-07-18 |
| PL203074B1 (pl) | 2009-08-31 |
| PH12000002167B1 (en) | 2008-10-28 |
| BR0017310A (pt) | 2003-07-08 |
| IN2005DE05932A (enrdf_load_stackoverflow) | 2008-05-09 |
| HUP0300723A3 (en) | 2006-06-28 |
| HUP0300723A2 (hu) | 2003-09-29 |
| PL362899A1 (en) | 2004-11-02 |
| BR0017310B1 (pt) | 2011-10-04 |
| TW591012B (en) | 2004-06-11 |
| AR025233A1 (es) | 2002-11-13 |
| IL154207A (en) | 2008-12-29 |
| AU2000264750A1 (en) | 2001-03-13 |
| WO2001012580A1 (fr) | 2001-02-22 |
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