CA1146977A - Process for the preparation of dihalovinyl compounds - Google Patents
Process for the preparation of dihalovinyl compoundsInfo
- Publication number
- CA1146977A CA1146977A CA000345474A CA345474A CA1146977A CA 1146977 A CA1146977 A CA 1146977A CA 000345474 A CA000345474 A CA 000345474A CA 345474 A CA345474 A CA 345474A CA 1146977 A CA1146977 A CA 1146977A
- Authority
- CA
- Canada
- Prior art keywords
- group
- methyl
- process according
- formula
- zinc
- 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.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 32
- 238000000034 method Methods 0.000 title claims abstract description 15
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims abstract description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 14
- 239000011701 zinc Substances 0.000 claims abstract description 13
- 229910052725 zinc Inorganic materials 0.000 claims abstract description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 12
- -1 tri-halomethyl compound Chemical class 0.000 claims abstract description 6
- 239000002253 acid Substances 0.000 claims abstract description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 4
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 4
- 239000000460 chlorine Substances 0.000 claims abstract description 4
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 4
- 125000001559 cyclopropyl group Chemical class [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 3
- 125000005843 halogen group Chemical group 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 5
- 239000000543 intermediate Substances 0.000 abstract description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 239000002917 insecticide Substances 0.000 abstract description 2
- 239000002728 pyrethroid Substances 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 229960000583 acetic acid Drugs 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000012362 glacial acetic acid Substances 0.000 description 6
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 229960000443 hydrochloric acid Drugs 0.000 description 5
- 235000011167 hydrochloric acid Nutrition 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 4
- VEMKTZHHVJILDY-UXHICEINSA-N bioresmethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UXHICEINSA-N 0.000 description 4
- FXHGMKSSBGDXIY-UHFFFAOYSA-N heptanal Chemical compound CCCCCCC=O FXHGMKSSBGDXIY-UHFFFAOYSA-N 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- 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 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SAQSTQBVENFSKT-UHFFFAOYSA-M TCA-sodium Chemical compound [Na+].[O-]C(=O)C(Cl)(Cl)Cl SAQSTQBVENFSKT-UHFFFAOYSA-M 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000001728 carbonyl compounds Chemical class 0.000 description 2
- 125000000113 cyclohexyl group Chemical class [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- NPXUKNQBFIIIDW-UHFFFAOYSA-N dichlorophosphinite Chemical compound [O-]P(Cl)Cl NPXUKNQBFIIIDW-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- JJRVKDKJXZCFAQ-UHFFFAOYSA-N methyl (1,1,1-trichloro-3-methylbutan-2-yl) carbonate Chemical compound COC(=O)OC(C(C)C)C(Cl)(Cl)Cl JJRVKDKJXZCFAQ-UHFFFAOYSA-N 0.000 description 2
- CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- OBWOEYSBRMRKHI-UHFFFAOYSA-N (1,1,1-tribromo-3-methylbutan-2-yl) acetate Chemical compound CC(C)C(C(Br)(Br)Br)OC(C)=O OBWOEYSBRMRKHI-UHFFFAOYSA-N 0.000 description 1
- YSLRNSJUAJXAPT-UHFFFAOYSA-N (1,1,1-trichloro-4-methylpent-3-en-2-yl) acetate Chemical compound CC(C)=CC(C(Cl)(Cl)Cl)OC(C)=O YSLRNSJUAJXAPT-UHFFFAOYSA-N 0.000 description 1
- ZFIHZJPVRVOBFF-UHFFFAOYSA-N (1,1,1-trichloro-4-methylpent-4-en-2-yl) acetate Chemical compound CC(=C)CC(C(Cl)(Cl)Cl)OC(C)=O ZFIHZJPVRVOBFF-UHFFFAOYSA-N 0.000 description 1
- QXRXCEKPGOHKKN-UHFFFAOYSA-N 1,1,1-tribromo-3-methylbutan-2-ol Chemical compound CC(C)C(O)C(Br)(Br)Br QXRXCEKPGOHKKN-UHFFFAOYSA-N 0.000 description 1
- KHNONEOSYSRKHI-UHFFFAOYSA-N 1,1,1-trichlorooctan-2-ol Chemical compound CCCCCCC(O)C(Cl)(Cl)Cl KHNONEOSYSRKHI-UHFFFAOYSA-N 0.000 description 1
- FWWDARKGGUNRPN-UHFFFAOYSA-N 1,1-dichloro-3-methylbut-1-ene Chemical compound CC(C)C=C(Cl)Cl FWWDARKGGUNRPN-UHFFFAOYSA-N 0.000 description 1
- 125000004917 3-methyl-2-butyl group Chemical group CC(C(C)*)C 0.000 description 1
- XPYQFIISZQCINN-QVXDJYSKSA-N 4-amino-1-[(2r,3e,4s,5r)-3-(fluoromethylidene)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one;hydrate Chemical compound O.O=C1N=C(N)C=CN1[C@H]1C(=C/F)/[C@H](O)[C@@H](CO)O1 XPYQFIISZQCINN-QVXDJYSKSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
- 241001024304 Mino Species 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 241000610375 Sparisoma viride Species 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- CXXBSOUOOQDXOR-UHFFFAOYSA-N dibromo(1,1,1-trichlorooctan-2-yloxy)phosphane Chemical compound CCCCCCC(C(Cl)(Cl)Cl)OP(Br)Br CXXBSOUOOQDXOR-UHFFFAOYSA-N 0.000 description 1
- GQFUMGWNGFCEOR-UHFFFAOYSA-N dichloro(1,1,1-trichlorooctan-2-yloxy)phosphane Chemical compound CCCCCCC(C(Cl)(Cl)Cl)OP(Cl)Cl GQFUMGWNGFCEOR-UHFFFAOYSA-N 0.000 description 1
- PVCINRPAXRJLEP-UHFFFAOYSA-N dichloro(ethoxy)phosphane Chemical compound CCOP(Cl)Cl PVCINRPAXRJLEP-UHFFFAOYSA-N 0.000 description 1
- BCYROXNMOOWCIJ-UHFFFAOYSA-N dichloro-(1,1,1-tribromo-3-methylbutan-2-yl)oxyphosphane Chemical compound CC(C)C(C(Br)(Br)Br)OP(Cl)Cl BCYROXNMOOWCIJ-UHFFFAOYSA-N 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 231100001225 mammalian toxicity Toxicity 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- BBNMJOFVKHQBIA-UHFFFAOYSA-N methyl (1,1,1-tribromo-3-methylbutan-2-yl) carbonate Chemical compound COC(=O)OC(C(C)C)C(Br)(Br)Br BBNMJOFVKHQBIA-UHFFFAOYSA-N 0.000 description 1
- AURAIVQQWTUVJH-UHFFFAOYSA-N methyl (1,1,1-trichloro-2-methylbutan-2-yl) carbonate Chemical compound CCC(C)(C(Cl)(Cl)Cl)OC(=O)OC AURAIVQQWTUVJH-UHFFFAOYSA-N 0.000 description 1
- QICLHXAZHZLGTI-UHFFFAOYSA-N methyl (1,1,1-trichloro-2-methylpropan-2-yl) carbonate Chemical compound COC(=O)OC(C)(C)C(Cl)(Cl)Cl QICLHXAZHZLGTI-UHFFFAOYSA-N 0.000 description 1
- IFPIYRWVNHBJCW-UHFFFAOYSA-N methyl 1,1,1-trichloro-3-methylbutane-2-sulfonate Chemical compound COS(=O)(=O)C(C(C)C)C(Cl)(Cl)Cl IFPIYRWVNHBJCW-UHFFFAOYSA-N 0.000 description 1
- ZPDIVJBYDYEDMA-UHFFFAOYSA-N methyl 1,1,1-trichlorooctan-2-yl carbonate Chemical compound CCCCCCC(C(Cl)(Cl)Cl)OC(=O)OC ZPDIVJBYDYEDMA-UHFFFAOYSA-N 0.000 description 1
- YSRFKDJOSXXMHP-UHFFFAOYSA-N methyl 2,2-dimethyl-3-(2,2,2-trichloro-1-hydroxyethyl)cyclopropane-1-carboxylate Chemical compound COC(=O)C1C(C(O)C(Cl)(Cl)Cl)C1(C)C YSRFKDJOSXXMHP-UHFFFAOYSA-N 0.000 description 1
- NYXWLDBEESHLPU-UHFFFAOYSA-N methyl [1-(trichloromethyl)cyclohexyl] carbonate Chemical compound COC(=O)OC1(C(Cl)(Cl)Cl)CCCCC1 NYXWLDBEESHLPU-UHFFFAOYSA-N 0.000 description 1
- AQIXEPGDORPWBJ-UHFFFAOYSA-N pentan-3-ol Chemical compound CCC(O)CC AQIXEPGDORPWBJ-UHFFFAOYSA-N 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical class OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- LNGWMJGSTQQAJJ-UHFFFAOYSA-M potassium;1,1,1-trichlorooctan-2-yl carbonate Chemical compound [K+].CCCCCCC(C(Cl)(Cl)Cl)OC([O-])=O LNGWMJGSTQQAJJ-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-M trichloroacetate Chemical compound [O-]C(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-M 0.000 description 1
- 229940066528 trichloroacetate Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7910662 | 1979-03-27 | ||
| GB7910662 | 1979-03-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1146977A true CA1146977A (en) | 1983-05-24 |
Family
ID=10504160
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000345474A Expired CA1146977A (en) | 1979-03-27 | 1980-02-13 | Process for the preparation of dihalovinyl compounds |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4307243A (ref) |
| EP (1) | EP0016505B1 (ref) |
| JP (1) | JPS55130925A (ref) |
| AR (1) | AR226306A1 (ref) |
| AU (1) | AU538452B2 (ref) |
| BR (1) | BR8001784A (ref) |
| CA (1) | CA1146977A (ref) |
| DE (1) | DE3062394D1 (ref) |
| DK (1) | DK128780A (ref) |
| ES (1) | ES489878A0 (ref) |
| HU (1) | HU183165B (ref) |
| IN (1) | IN154013B (ref) |
| PL (1) | PL120432B1 (ref) |
| ZA (1) | ZA801772B (ref) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU183505B (en) * | 1981-07-03 | 1984-05-28 | Chinoin Gyogyszer Es Vegyeszet | Process for cleaving 1-substituted 2,2,2-trihalogenoethyl-esters |
| JPH0674238B2 (ja) * | 1985-09-30 | 1994-09-21 | 財団法人相模中央化学研究所 | ２，２−ジメチルシクロプロパンカルボン酸誘導体 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3345420A (en) * | 1963-12-13 | 1967-10-03 | Union Carbide Corp | 1, 1, 3, 3-tetrahalo-2, 2, 4, 4-tetramethylcyclobutanes |
| GB1480671A (en) * | 1975-04-17 | 1977-07-20 | Ici Ltd | Process for the preparation of 1,1-dihalo-4-methyl pentadienes |
| US4289711A (en) * | 1975-09-05 | 1981-09-15 | Burroughs Wellcome Co. | Ester synthesis |
| JPS5273843A (en) * | 1975-12-17 | 1977-06-21 | Sumitomo Chem Co Ltd | Preparation of 2,2-dimethyl-3-trihalogeno-acetylcyclopropane carboxyli c acid derivatives |
| JPS5273842A (en) * | 1975-12-18 | 1977-06-21 | Sumitomo Chem Co Ltd | Preparation of 2,2-dimethyl-3-)alpha-hydroxy-alphe-trihalogenomethylme thyl) -cyclopropane carboxylic acid derivatives |
-
1980
- 1980-02-13 CA CA000345474A patent/CA1146977A/en not_active Expired
- 1980-03-14 EP EP80200241A patent/EP0016505B1/en not_active Expired
- 1980-03-14 DE DE8080200241T patent/DE3062394D1/de not_active Expired
- 1980-03-25 DK DK128780A patent/DK128780A/da not_active Application Discontinuation
- 1980-03-25 JP JP3700380A patent/JPS55130925A/ja active Granted
- 1980-03-25 AR AR280430A patent/AR226306A1/es active
- 1980-03-25 US US06/134,022 patent/US4307243A/en not_active Expired - Lifetime
- 1980-03-25 HU HU80692A patent/HU183165B/hu unknown
- 1980-03-25 ES ES489878A patent/ES489878A0/es active Granted
- 1980-03-25 IN IN219/DEL/80A patent/IN154013B/en unknown
- 1980-03-25 ZA ZA00801772A patent/ZA801772B/xx unknown
- 1980-03-25 AU AU56809/80A patent/AU538452B2/en not_active Ceased
- 1980-03-25 BR BR8001784A patent/BR8001784A/pt not_active IP Right Cessation
- 1980-03-25 PL PL1980222996A patent/PL120432B1/pl unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HU183165B (en) | 1984-04-28 |
| AU5680980A (en) | 1980-10-02 |
| PL120432B1 (en) | 1982-02-27 |
| IN154013B (ref) | 1984-09-08 |
| BR8001784A (pt) | 1980-11-18 |
| ZA801772B (en) | 1981-03-25 |
| PL222996A1 (ref) | 1980-12-15 |
| ES8104164A1 (es) | 1981-04-16 |
| AR226306A1 (es) | 1982-06-30 |
| DE3062394D1 (en) | 1983-04-28 |
| ES489878A0 (es) | 1981-04-16 |
| EP0016505B1 (en) | 1983-03-23 |
| EP0016505A1 (en) | 1980-10-01 |
| DK128780A (da) | 1980-09-28 |
| US4307243A (en) | 1981-12-22 |
| JPS6323975B2 (ref) | 1988-05-18 |
| JPS55130925A (en) | 1980-10-11 |
| AU538452B2 (en) | 1984-08-16 |
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