WO2001012580A1 - Process for the preparation of 5-[(4-chlorophenyl)-methyl]-2,2-dimethylcyclopentanone - Google Patents
Process for the preparation of 5-[(4-chlorophenyl)-methyl]-2,2-dimethylcyclopentanone Download PDFInfo
- Publication number
- WO2001012580A1 WO2001012580A1 PCT/JP2000/005401 JP0005401W WO0112580A1 WO 2001012580 A1 WO2001012580 A1 WO 2001012580A1 JP 0005401 W JP0005401 W JP 0005401W WO 0112580 A1 WO0112580 A1 WO 0112580A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- methyl
- chlorophenyl
- oxocyclopentanecarboxylate
- dimethyl
- ethyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 16
- 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 description 7
- -1 methyl halide Chemical class 0.000 claims abstract description 38
- 238000004519 manufacturing process Methods 0.000 claims abstract description 32
- 239000005868 Metconazole Substances 0.000 claims abstract description 10
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000000417 fungicide Substances 0.000 claims abstract description 10
- XWPZUHJBOLQNMN-UHFFFAOYSA-N metconazole Chemical compound C1=NC=NN1CC1(O)C(C)(C)CCC1CC1=CC=C(Cl)C=C1 XWPZUHJBOLQNMN-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000012312 sodium hydride Substances 0.000 claims abstract description 10
- 229910000104 sodium hydride Inorganic materials 0.000 claims abstract description 10
- 230000000855 fungicidal effect Effects 0.000 claims abstract description 9
- 230000007062 hydrolysis Effects 0.000 claims abstract description 5
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 96
- 238000006243 chemical reaction Methods 0.000 claims description 63
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 62
- 229910052751 metal Inorganic materials 0.000 claims description 20
- 239000002184 metal Substances 0.000 claims description 20
- UDSFAEKRVUSQDD-UHFFFAOYSA-N Dimethyl adipate Chemical compound COC(=O)CCCCC(=O)OC UDSFAEKRVUSQDD-UHFFFAOYSA-N 0.000 claims description 18
- 150000004703 alkoxides Chemical class 0.000 claims description 11
- 229960002944 cyclofenil Drugs 0.000 claims description 11
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- JQZAEUFPPSRDOP-UHFFFAOYSA-N 1-chloro-4-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C=C1 JQZAEUFPPSRDOP-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- FTGZMZBYOHMEPS-UHFFFAOYSA-N 2,2-dimethylcyclopentan-1-one Chemical compound CC1(C)CCCC1=O FTGZMZBYOHMEPS-UHFFFAOYSA-N 0.000 claims description 5
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 claims description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 2
- IIHIJFJSXPDTNO-UHFFFAOYSA-N methyl cyclopentanecarboxylate Chemical compound COC(=O)C1CCCC1 IIHIJFJSXPDTNO-UHFFFAOYSA-N 0.000 claims description 2
- JHZPNBKZPAWCJD-UHFFFAOYSA-N ethyl 2-oxocyclopentane-1-carboxylate Chemical compound CCOC(=O)C1CCCC1=O JHZPNBKZPAWCJD-UHFFFAOYSA-N 0.000 claims 3
- DMHZDOTYAVHSEH-UHFFFAOYSA-N 1-(chloromethyl)-4-methylbenzene Chemical compound CC1=CC=C(CCl)C=C1 DMHZDOTYAVHSEH-UHFFFAOYSA-N 0.000 claims 1
- SNPWJRNYYANSRB-UHFFFAOYSA-N 1-[(4-chlorophenyl)methyl]-3-methyl-2-oxocyclopentane-1-carboxylic acid Chemical compound O=C1C(C)CCC1(C(O)=O)CC1=CC=C(Cl)C=C1 SNPWJRNYYANSRB-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 150000007942 carboxylates Chemical class 0.000 claims 1
- JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentanecarboxylic acid Chemical compound OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 claims 1
- ORLZPOSPUFSCMW-UHFFFAOYSA-N ethyl 3,3-dimethyl-2-oxocyclopentane-1-carboxylate Chemical compound CCOC(=O)C1CCC(C)(C)C1=O ORLZPOSPUFSCMW-UHFFFAOYSA-N 0.000 claims 1
- YBEUXWGGKSZODV-UHFFFAOYSA-N ethyl 5-oxocyclopentene-1-carboxylate Chemical compound CCOC(=O)C1=CCCC1=O YBEUXWGGKSZODV-UHFFFAOYSA-N 0.000 claims 1
- 125000004494 ethyl ester group Chemical group 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- OGIKPUCMXHEUMK-UHFFFAOYSA-N tert-butyl 2-oxocyclopentane-1-carboxylate Chemical compound CC(C)(C)OC(=O)C1CCCC1=O OGIKPUCMXHEUMK-UHFFFAOYSA-N 0.000 claims 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 description 3
- QGUHMUXBDNKLNM-UHFFFAOYSA-N methyl 1-[(4-chlorophenyl)methyl]-3,3-dimethyl-2-oxocyclopentane-1-carboxylate Chemical compound C=1C=C(Cl)C=CC=1CC1(C(=O)OC)CCC(C)(C)C1=O QGUHMUXBDNKLNM-UHFFFAOYSA-N 0.000 abstract description 2
- VHDUPMOJGBENBV-UHFFFAOYSA-N ethyl 1-[(4-chlorophenyl)methyl]-3,3-dimethyl-2-oxocyclopentane-1-carboxylate Chemical compound C=1C=C(Cl)C=CC=1CC1(C(=O)OCC)CCC(C)(C)C1=O VHDUPMOJGBENBV-UHFFFAOYSA-N 0.000 abstract 1
- 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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
- 239000002904 solvent Substances 0.000 description 22
- 150000001875 compounds Chemical class 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 14
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- 230000007423 decrease Effects 0.000 description 7
- 229940102396 methyl bromide Drugs 0.000 description 7
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
- PZBBESSUKAHBHD-UHFFFAOYSA-N methyl 2-oxocyclopentane-1-carboxylate Chemical compound COC(=O)C1CCCC1=O PZBBESSUKAHBHD-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 4
- 238000004817 gas chromatography Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 239000002798 polar solvent Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- HLQZCRVEEQKNMS-UHFFFAOYSA-N 1-(chloromethyl)-4-phenylbenzene Chemical compound C1=CC(CCl)=CC=C1C1=CC=CC=C1 HLQZCRVEEQKNMS-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
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 150000001491 aromatic compounds Chemical class 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
- 238000005259 measurement Methods 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
- 239000002002 slurry Substances 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 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
- QZURFQCUAZFMSV-UHFFFAOYSA-N C(=O)(OC)C1C(CCC1)=O.[Na] Chemical compound C(=O)(OC)C1C(CCC1)=O.[Na] QZURFQCUAZFMSV-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 239000000010 aprotic solvent Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 2
- 230000008034 disappearance Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- TZHZMYGNHVTEFA-UHFFFAOYSA-N methyl 1-methyl-2-oxocyclopentane-1-carboxylate Chemical compound COC(=O)C1(C)CCCC1=O TZHZMYGNHVTEFA-UHFFFAOYSA-N 0.000 description 2
- 229940050176 methyl chloride Drugs 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 238000001577 simple distillation Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 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
- GQFNCVHPAIWUFJ-UHFFFAOYSA-N 3-[(4-chlorophenyl)methyl]-2,2-dimethylcyclopentan-1-one Chemical compound ClC1=CC=C(C=C1)CC1C(C(CC1)=O)(C)C GQFNCVHPAIWUFJ-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
- DPBQIRNFTKVJPK-UHFFFAOYSA-N 3-methyl-2-oxocyclopentane-1-carboxylic acid Chemical compound CC1CCC(C(O)=O)C1=O DPBQIRNFTKVJPK-UHFFFAOYSA-N 0.000 description 1
- ZCODXJQJFVYHSG-UHFFFAOYSA-N CC1(CCC(=C1)CC2=CC=C(C=C2)Cl)C Chemical class CC1(CCC(=C1)CC2=CC=C(C=C2)Cl)C ZCODXJQJFVYHSG-UHFFFAOYSA-N 0.000 description 1
- HEYNUKXGQVTHAD-UHFFFAOYSA-N CC1CCC(=O)C1CC2=CC=C(C=C2)Cl Chemical compound CC1CCC(=O)C1CC2=CC=C(C=C2)Cl HEYNUKXGQVTHAD-UHFFFAOYSA-N 0.000 description 1
- PIDXJHBKNROJFM-UHFFFAOYSA-N COC(=O)CCCCC(=O)OC.CCOC(=O)CCCCC(=O)OCC Chemical compound COC(=O)CCCCC(=O)OC.CCOC(=O)CCCCC(=O)OCC PIDXJHBKNROJFM-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- JBQLQIMCKFDOHK-UHFFFAOYSA-N Stephanol Natural products CC(O)C1(O)CCC2(O)C3(O)CC=C4CC(O)CCC4(C)C3C(O)C(O)C12C JBQLQIMCKFDOHK-UHFFFAOYSA-N 0.000 description 1
- XJWGVBQKHKZLIC-UHFFFAOYSA-N [Na].CC1C(C(CC1)C(=O)OC)=O Chemical compound [Na].CC1C(C(CC1)C(=O)OC)=O XJWGVBQKHKZLIC-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 210000000540 fraction c Anatomy 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- NUKZAGXMHTUAFE-UHFFFAOYSA-N methyl hexanoate Chemical compound CCCCCC(=O)OC NUKZAGXMHTUAFE-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- UOBSVARXACCLLH-UHFFFAOYSA-N monomethyl adipate Chemical compound COC(=O)CCCCC(O)=O UOBSVARXACCLLH-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- HSFQBFMEWSTNOW-UHFFFAOYSA-N sodium;carbanide Chemical group [CH3-].[Na+] HSFQBFMEWSTNOW-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 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
Abstract
Description
Claims
Priority Applications (14)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CZ20030664A CZ303562B6 (en) | 2000-08-11 | 2000-08-11 | Process for preparing 5-[(4-chlorophenyl)methyl]-2,2-diemethyl cyclopentanone |
PL362899A PL203074B1 (en) | 1999-08-13 | 2000-08-11 | Process for the preparation of 5−[(4−chlorophenyl)−methyl]−2,2−dimethylcyclopentanone |
BRPI0017310-0A BR0017310B1 (en) | 1999-08-13 | 2000-08-11 | process for producing 5 - [(4-chlorophenyl) methyl] -2,2-dimethylcyclopentanone. |
JP2001516881A JP4979170B2 (en) | 1999-08-13 | 2000-08-11 | Process for producing 5-[(4-chlorophenyl) methyl] -2,2-dimethylcyclopentanone |
US10/332,471 US7166750B1 (en) | 2000-08-11 | 2000-08-11 | Process for the preparation of 5-[(4-chlorophenyl)methyl]-2,2-dimethylcyclopentanone |
DE60031454T DE60031454T2 (en) | 2000-08-11 | 2000-08-11 | PROCESS FOR PREPARING 5- (4-CHLOROPHENYL) -METHYL-2,2-DIMETHYLCYCLOPENTANONE |
KR1020037001725A KR100697737B1 (en) | 2000-08-11 | 2000-08-11 | Process for the preparation of 5-[4-chlorophenyl)-methyl]-2, 2-dimethylcyclopentanone |
EP00951956A EP1308432B1 (en) | 2000-08-11 | 2000-08-11 | Process for the preparation of 5- (4-chlorophenyl)-methyl|-2,2-dimethylcyclopentanone |
IL15420700A IL154207A0 (en) | 2000-08-11 | 2000-08-11 | Process for the preparation of 5-[(4-chlorophenyl)-methyl]-2,2-dimethylcyclopentanone |
CNB008198101A CN1196665C (en) | 2000-08-11 | 2000-08-11 | Process for the preparation of 5-[4-chlorophenyl)-methyl]-2, 2-dimethylcyclopentanone |
AU2000264750A AU2000264750A1 (en) | 1999-08-13 | 2000-08-11 | Process for the preparation of 5-[(4-chlorophenyl)-methyl]-2,2-dimethylcyclopentanone |
HU0300723A HUP0300723A3 (en) | 1999-08-13 | 2000-08-11 | Process for the preparation of 5-[(4-chlorophenyl)-methyl]-2,2-dimethylcylopentanone |
UA2003021098A UA73364C2 (en) | 1999-08-13 | 2000-11-08 | A method for the preparation of 5-[(4-chlorophenyl)methyl]-2,2-dimethylcyclopentanone and a method for the preparation of intermediary compounds (variants) |
IL154207A IL154207A (en) | 1999-08-13 | 2003-01-30 | Process for the preparation of 5 - [(4 - chlorophenyl) - methyl] - 2, 2 - dimethylcyclopentanone |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP11/264292 | 1999-08-13 | ||
JP26429299 | 1999-08-13 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2001012580A1 true WO2001012580A1 (en) | 2001-02-22 |
Family
ID=17401150
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP2000/005401 WO2001012580A1 (en) | 1999-08-13 | 2000-08-11 | Process for the preparation of 5-[(4-chlorophenyl)-methyl]-2,2-dimethylcyclopentanone |
Country Status (12)
Country | Link |
---|---|
JP (1) | JP4979170B2 (en) |
AR (1) | AR025233A1 (en) |
AU (1) | AU2000264750A1 (en) |
BR (1) | BR0017310B1 (en) |
HU (1) | HUP0300723A3 (en) |
IL (1) | IL154207A (en) |
IN (1) | IN2005DE05932A (en) |
PH (1) | PH12000002167B1 (en) |
PL (1) | PL203074B1 (en) |
TW (1) | TW591012B (en) |
UA (1) | UA73364C2 (en) |
WO (1) | WO2001012580A1 (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2012169468A1 (en) | 2011-06-07 | 2012-12-13 | 株式会社クレハ | Method for producing cyclopentanone compound, and intermediate compound |
WO2015075981A1 (en) * | 2013-11-22 | 2015-05-28 | 株式会社クレハ | Method for producing carbonyl compound |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0267778A2 (en) * | 1986-11-10 | 1988-05-18 | Kureha Kagaku Kogyo Kabushiki Kaisha | Azole derivatives useful in controlling plant diseases and regulating plant growth |
EP0413448A1 (en) * | 1989-08-15 | 1991-02-20 | Kureha Kagaku Kogyo Kabushiki Kaisha | An Azole-substituted cycloalkanol derivative, a process to produce the same and a use of the derivative as an agricultural and horticultural fungicide |
EP0537909A1 (en) * | 1991-09-18 | 1993-04-21 | Kureha Chemical Industry Co., Ltd. | 3-(Unsubstituted or substituted benzyl)-1-alkyl-2-oxocyclopentane carboxylic acid alkyl ester derivatives, and their preparation and use |
EP0731083A1 (en) * | 1995-03-10 | 1996-09-11 | Kureha Kagaku Kogyo Kabushiki Kaisha | Process for the producing of alkylcyclopentanone derivatives |
-
2000
- 2000-08-09 TW TW089116041A patent/TW591012B/en not_active IP Right Cessation
- 2000-08-11 PL PL362899A patent/PL203074B1/en unknown
- 2000-08-11 BR BRPI0017310-0A patent/BR0017310B1/en not_active IP Right Cessation
- 2000-08-11 JP JP2001516881A patent/JP4979170B2/en not_active Expired - Lifetime
- 2000-08-11 WO PCT/JP2000/005401 patent/WO2001012580A1/en active IP Right Grant
- 2000-08-11 HU HU0300723A patent/HUP0300723A3/en unknown
- 2000-08-11 AR ARP000104172A patent/AR025233A1/en not_active Application Discontinuation
- 2000-08-11 PH PH12000002167A patent/PH12000002167B1/en unknown
- 2000-08-11 AU AU2000264750A patent/AU2000264750A1/en not_active Abandoned
- 2000-11-08 UA UA2003021098A patent/UA73364C2/en 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
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0267778A2 (en) * | 1986-11-10 | 1988-05-18 | Kureha Kagaku Kogyo Kabushiki Kaisha | Azole derivatives useful in controlling plant diseases and regulating plant growth |
EP0413448A1 (en) * | 1989-08-15 | 1991-02-20 | Kureha Kagaku Kogyo Kabushiki Kaisha | An Azole-substituted cycloalkanol derivative, a process to produce the same and a use of the derivative as an agricultural and horticultural fungicide |
EP0537909A1 (en) * | 1991-09-18 | 1993-04-21 | Kureha Chemical Industry Co., Ltd. | 3-(Unsubstituted or substituted benzyl)-1-alkyl-2-oxocyclopentane carboxylic acid alkyl ester derivatives, and their preparation and use |
EP0731083A1 (en) * | 1995-03-10 | 1996-09-11 | Kureha Kagaku Kogyo Kabushiki Kaisha | Process for the producing of alkylcyclopentanone derivatives |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2012169468A1 (en) | 2011-06-07 | 2012-12-13 | 株式会社クレハ | Method for producing cyclopentanone compound, and intermediate compound |
JPWO2012169468A1 (en) * | 2011-06-07 | 2015-02-23 | 株式会社クレハ | Method for producing cyclopentanone compound and intermediate compound |
US8975434B2 (en) | 2011-06-07 | 2015-03-10 | Kureha Corporation | Method for producing cyclopentanone compound, and intermediate compound |
WO2015075981A1 (en) * | 2013-11-22 | 2015-05-28 | 株式会社クレハ | Method for producing carbonyl compound |
Also Published As
Publication number | Publication date |
---|---|
BR0017310B1 (en) | 2011-10-04 |
JPWO0112580A1 (en) | 2003-03-11 |
JP4979170B2 (en) | 2012-07-18 |
TW591012B (en) | 2004-06-11 |
HUP0300723A2 (en) | 2003-09-29 |
PL203074B1 (en) | 2009-08-31 |
HUP0300723A3 (en) | 2006-06-28 |
UA73364C2 (en) | 2005-07-15 |
AR025233A1 (en) | 2002-11-13 |
PL362899A1 (en) | 2004-11-02 |
BR0017310A (en) | 2003-07-08 |
PH12000002167B1 (en) | 2008-10-28 |
AU2000264750A1 (en) | 2001-03-13 |
IN2005DE05932A (en) | 2008-05-09 |
IL154207A (en) | 2008-12-29 |
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