JP2003531880A - ハロゲン化ヒドロキシジフェニル化合物の調製方法 - Google Patents
ハロゲン化ヒドロキシジフェニル化合物の調製方法Info
- Publication number
- JP2003531880A JP2003531880A JP2001580851A JP2001580851A JP2003531880A JP 2003531880 A JP2003531880 A JP 2003531880A JP 2001580851 A JP2001580851 A JP 2001580851A JP 2001580851 A JP2001580851 A JP 2001580851A JP 2003531880 A JP2003531880 A JP 2003531880A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- formula
- acid
- reaction
- carried out
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 31
- 238000000034 method Methods 0.000 title claims abstract description 21
- 238000006243 chemical reaction Methods 0.000 claims abstract description 34
- -1 halogenated benzene compound Chemical class 0.000 claims abstract description 12
- 239000010949 copper Substances 0.000 claims abstract description 8
- 150000002989 phenols Chemical class 0.000 claims abstract description 8
- 229910052802 copper Inorganic materials 0.000 claims abstract description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000003054 catalyst Substances 0.000 claims abstract description 5
- 239000011368 organic material Substances 0.000 claims abstract description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims abstract description 3
- 230000003301 hydrolyzing effect Effects 0.000 claims abstract 2
- 239000000203 mixture Substances 0.000 claims description 29
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 21
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 16
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 15
- 238000002360 preparation method Methods 0.000 claims description 14
- 230000003647 oxidation Effects 0.000 claims description 8
- 238000007254 oxidation reaction Methods 0.000 claims description 8
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 claims description 6
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 claims description 6
- 239000002841 Lewis acid Substances 0.000 claims description 4
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims description 4
- 239000012346 acetyl chloride Substances 0.000 claims description 4
- 150000007517 lewis acids Chemical class 0.000 claims description 4
- 238000005917 acylation reaction Methods 0.000 claims description 3
- 239000000645 desinfectant Substances 0.000 claims description 3
- 150000001266 acyl halides Chemical class 0.000 claims description 2
- 230000000813 microbial effect Effects 0.000 claims description 2
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 claims 1
- SCKXCAADGDQQCS-UHFFFAOYSA-N Performic acid Chemical compound OOC=O SCKXCAADGDQQCS-UHFFFAOYSA-N 0.000 claims 1
- IYKMJEUFFZDRLS-UHFFFAOYSA-N n-(1-phenylethyl)cyclopropanamine Chemical compound C=1C=CC=CC=1C(C)NC1CC1 IYKMJEUFFZDRLS-UHFFFAOYSA-N 0.000 claims 1
- 244000005700 microbiome Species 0.000 abstract description 3
- 230000001590 oxidative effect Effects 0.000 abstract description 2
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 9
- 239000012071 phase Substances 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- CYNFEPKQDJHIMV-UHFFFAOYSA-N 1-(2,5-dichlorophenyl)ethanone Chemical compound CC(=O)C1=CC(Cl)=CC=C1Cl CYNFEPKQDJHIMV-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- 150000003738 xylenes Chemical class 0.000 description 3
- KFHHPVVJLXPHJL-UPHRSURJSA-N (z)-4-hydroperoxy-4-oxobut-2-enoic acid Chemical compound OOC(=O)\C=C/C(O)=O KFHHPVVJLXPHJL-UPHRSURJSA-N 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 2
- RVZFFCSCPXYAPX-UHFFFAOYSA-N 1-[5-chloro-2-(2,4-dichlorophenoxy)phenyl]ethanone Chemical compound CC(=O)C1=CC(Cl)=CC=C1OC1=CC=C(Cl)C=C1Cl RVZFFCSCPXYAPX-UHFFFAOYSA-N 0.000 description 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 2
- LULAYUGMBFYYEX-UHFFFAOYSA-N 3-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- XEFQLINVKFYRCS-UHFFFAOYSA-N Triclosan Chemical compound OC1=CC(Cl)=CC=C1OC1=CC=C(Cl)C=C1Cl XEFQLINVKFYRCS-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 238000010751 Ullmann type reaction Methods 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 229940116318 copper carbonate Drugs 0.000 description 2
- BERDEBHAJNAUOM-UHFFFAOYSA-N copper(i) oxide Chemical compound [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 description 2
- GEZOTWYUIKXWOA-UHFFFAOYSA-L copper;carbonate Chemical compound [Cu+2].[O-]C([O-])=O GEZOTWYUIKXWOA-UHFFFAOYSA-L 0.000 description 2
- JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 description 2
- BYNQFCJOHGOKSS-UHFFFAOYSA-N diclosan Chemical compound OC1=CC(Cl)=CC=C1OC1=CC=C(Cl)C=C1 BYNQFCJOHGOKSS-UHFFFAOYSA-N 0.000 description 2
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
- 102100022005 B-lymphocyte antigen CD20 Human genes 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 102100024522 Bladder cancer-associated protein Human genes 0.000 description 1
- 101150110835 Blcap gene Proteins 0.000 description 1
- 238000006418 Brown reaction Methods 0.000 description 1
- 241000282461 Canis lupus Species 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- 101000897405 Homo sapiens B-lymphocyte antigen CD20 Proteins 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
- 101100015456 Litomosoides carinii GP22 gene Proteins 0.000 description 1
- 229920000305 Nylon 6,10 Polymers 0.000 description 1
- 101100493740 Oryza sativa subsp. japonica BC10 gene Proteins 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 238000006887 Ullmann reaction Methods 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- YVKQDASGCRLLKL-UHFFFAOYSA-N acetic acid;magnesium Chemical compound [Mg].CC(O)=O.CC(O)=O YVKQDASGCRLLKL-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000003855 acyl compounds Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 229910021538 borax Inorganic materials 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 229960005215 dichloroacetic acid Drugs 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical class [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
- 229910000342 sodium bisulfate Chemical class 0.000 description 1
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000000271 synthetic detergent Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 229960003500 triclosan Drugs 0.000 description 1
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
- 238000009736 wetting 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
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
-
- 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
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/26—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of hydroxy or O-metal 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
- C07C45/61—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
- C07C45/68—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 increase in the number of carbon atoms
- C07C45/70—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 increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
- C07C45/71—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 increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
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)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP00810382 | 2000-05-04 | ||
| EP00810382.2 | 2000-05-04 | ||
| PCT/EP2001/004710 WO2001083418A1 (en) | 2000-05-04 | 2001-04-26 | Process for the preparation of halogenated hydroxydiphenyl compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2003531880A true JP2003531880A (ja) | 2003-10-28 |
| JP2003531880A5 JP2003531880A5 (enExample) | 2008-07-31 |
Family
ID=8174677
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001580851A Withdrawn JP2003531880A (ja) | 2000-05-04 | 2001-04-26 | ハロゲン化ヒドロキシジフェニル化合物の調製方法 |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US6706930B2 (enExample) |
| EP (1) | EP1320516B1 (enExample) |
| JP (1) | JP2003531880A (enExample) |
| KR (1) | KR100801456B1 (enExample) |
| CN (1) | CN1285555C (enExample) |
| AR (1) | AR028400A1 (enExample) |
| AT (1) | ATE305913T1 (enExample) |
| AU (1) | AU2001260254A1 (enExample) |
| BR (1) | BR0110458B1 (enExample) |
| CZ (1) | CZ20023947A3 (enExample) |
| DE (1) | DE60113862T2 (enExample) |
| ES (1) | ES2249435T3 (enExample) |
| IL (1) | IL152057A0 (enExample) |
| MX (1) | MXPA02010291A (enExample) |
| RU (1) | RU2002131892A (enExample) |
| SK (1) | SK16912002A3 (enExample) |
| TW (1) | TWI274748B (enExample) |
| WO (1) | WO2001083418A1 (enExample) |
| ZA (1) | ZA200209631B (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20050266095A1 (en) * | 2004-06-01 | 2005-12-01 | Erning Xia | Gentle preservative compositions |
| CN104628537A (zh) * | 2015-02-03 | 2015-05-20 | 武汉工程大学 | 一种2,5-二氯苯酚的合成工艺 |
| CN109020935A (zh) * | 2018-10-11 | 2018-12-18 | 西安近代化学研究所 | 一种二苯并呋喃衍生物及其制备方法 |
| CN113045390A (zh) * | 2021-03-17 | 2021-06-29 | 枣庄市润安制药新材料有限公司 | 一种利用Baeyer-Villiger氧化制备二氯生的方法 |
| CN116589344B (zh) * | 2023-05-17 | 2025-03-07 | 梯尔希（南京）药物研发有限公司 | 一种氘标记二氯生的合成方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL123015A (en) | 1997-02-05 | 2003-07-06 | Ciba Sc Holding Ag | Process for the preparation of ortho-substituted halophenols, some new intermediates and disinfectants for protecting organic materials from attack by microorganisms comprising compounds prepared by said process |
| WO1999010310A1 (en) | 1997-08-29 | 1999-03-04 | The Dow Chemical Company | Process for producing diphenylethers and esters |
| US20020128522A1 (en) | 1998-10-06 | 2002-09-12 | Teodoro Armando Di | Process for the preparation of 4,4' -dihalogen-o-hydroxydiphenyl compounds |
-
2001
- 2001-04-09 TW TW090108566A patent/TWI274748B/zh not_active IP Right Cessation
- 2001-04-26 JP JP2001580851A patent/JP2003531880A/ja not_active Withdrawn
- 2001-04-26 DE DE60113862T patent/DE60113862T2/de not_active Expired - Lifetime
- 2001-04-26 IL IL15205701A patent/IL152057A0/xx unknown
- 2001-04-26 US US10/275,022 patent/US6706930B2/en not_active Expired - Fee Related
- 2001-04-26 RU RU2002131892/04A patent/RU2002131892A/ru not_active Application Discontinuation
- 2001-04-26 EP EP01933893A patent/EP1320516B1/en not_active Expired - Lifetime
- 2001-04-26 MX MXPA02010291A patent/MXPA02010291A/es active IP Right Grant
- 2001-04-26 AT AT01933893T patent/ATE305913T1/de not_active IP Right Cessation
- 2001-04-26 ES ES01933893T patent/ES2249435T3/es not_active Expired - Lifetime
- 2001-04-26 SK SK1691-2002A patent/SK16912002A3/sk unknown
- 2001-04-26 CN CNB01809001XA patent/CN1285555C/zh not_active Expired - Fee Related
- 2001-04-26 BR BRPI0110458-6A patent/BR0110458B1/pt not_active IP Right Cessation
- 2001-04-26 KR KR1020027014670A patent/KR100801456B1/ko not_active Expired - Fee Related
- 2001-04-26 AU AU2001260254A patent/AU2001260254A1/en not_active Abandoned
- 2001-04-26 CZ CZ20023947A patent/CZ20023947A3/cs unknown
- 2001-04-26 WO PCT/EP2001/004710 patent/WO2001083418A1/en not_active Ceased
- 2001-05-02 AR ARP010102071A patent/AR028400A1/es unknown
-
2002
- 2002-11-27 ZA ZA200209631A patent/ZA200209631B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ATE305913T1 (de) | 2005-10-15 |
| KR100801456B1 (ko) | 2008-02-11 |
| ZA200209631B (en) | 2003-10-23 |
| EP1320516A1 (en) | 2003-06-25 |
| WO2001083418A1 (en) | 2001-11-08 |
| CZ20023947A3 (cs) | 2003-03-12 |
| EP1320516B1 (en) | 2005-10-05 |
| US6706930B2 (en) | 2004-03-16 |
| TWI274748B (en) | 2007-03-01 |
| BR0110458B1 (pt) | 2012-06-12 |
| AR028400A1 (es) | 2003-05-07 |
| KR20020092464A (ko) | 2002-12-11 |
| CN1285555C (zh) | 2006-11-22 |
| US20030163005A1 (en) | 2003-08-28 |
| CN1427811A (zh) | 2003-07-02 |
| DE60113862D1 (de) | 2006-02-16 |
| BR0110458A (pt) | 2003-03-11 |
| DE60113862T2 (de) | 2006-04-27 |
| ES2249435T3 (es) | 2006-04-01 |
| MXPA02010291A (es) | 2003-04-25 |
| RU2002131892A (ru) | 2004-04-10 |
| SK16912002A3 (sk) | 2003-05-02 |
| IL152057A0 (en) | 2003-05-29 |
| AU2001260254A1 (en) | 2001-11-12 |
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