CS207797B2 - Method of making the derivatives of the clorstyrylpropan carboxyl acid - Google Patents

Method of making the derivatives of the clorstyrylpropan carboxyl acid Download PDF

Info

Publication number: CS207797B2
Authority: CS; Czechoslovakia
Prior art keywords: acid; formula; alkyl; chloro; mol
Prior art date: 1978-06-21

Application number

CS794247A

Other languages

Czech (cs)

English (en)

Inventor

Hans-Joachim Diehr

Rainer A Fuchs

Original Assignee

Bayer Ag

Priority date (The priority date 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 date listed.)

1978-06-21

Filing date

1979-06-20

Publication date

1981-08-31

1979-06-20 Application filed by Bayer Ag filed Critical Bayer Ag

1981-08-31 Publication of CS207797B2 publication Critical patent/CS207797B2/cs

Links

239000002253 acid Substances 0.000 title claims description 16
238000004519 manufacturing process Methods 0.000 title description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 title 1
238000000034 method Methods 0.000 claims abstract description 14
125000000217 alkyl group Chemical group 0.000 claims abstract description 11
CWTZPYRDNMWMMF-UHFFFAOYSA-N 2-chloro-1-(2-phenylethenyl)cyclopropane-1-carboxylic acid Chemical class C=1C=CC=CC=1C=CC1(C(=O)O)CC1Cl CWTZPYRDNMWMMF-UHFFFAOYSA-N 0.000 claims abstract description 8
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
239000001257 hydrogen Substances 0.000 claims abstract description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 5
238000002360 preparation method Methods 0.000 claims abstract description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 4
229910052736 halogen Chemical group 0.000 claims abstract description 4
150000002367 halogens Chemical group 0.000 claims abstract description 4
239000002904 solvent Substances 0.000 claims description 14
150000002148 esters Chemical class 0.000 claims description 8
150000001299 aldehydes Chemical class 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 6
238000006243 chemical reaction Methods 0.000 abstract description 10
239000003085 diluting agent Substances 0.000 abstract description 6
FKKZWEWQUQIZKF-UHFFFAOYSA-N [chloro(phenyl)methyl]phosphonic acid Chemical class OP(O)(=O)C(Cl)C1=CC=CC=C1 FKKZWEWQUQIZKF-UHFFFAOYSA-N 0.000 abstract description 3
229910052783 alkali metal Inorganic materials 0.000 abstract description 3
150000008044 alkali metal hydroxides Chemical class 0.000 abstract description 2
150000001340 alkali metals Chemical class 0.000 abstract description 2
SFDXJGBNXVTWEB-UHFFFAOYSA-N 1-formylcyclopropane-1-carboxylic acid Chemical class OC(=O)C1(C=O)CC1 SFDXJGBNXVTWEB-UHFFFAOYSA-N 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
150000001875 compounds Chemical class 0.000 description 17
239000011541 reaction mixture Substances 0.000 description 15
239000000203 mixture Substances 0.000 description 13
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
239000002585 base Substances 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 10
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
-1 diethyl α-chloro-4-fluorobenzylphosphonic acid Chemical compound 0.000 description 9
239000000243 solution Substances 0.000 description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
239000012074 organic phase Substances 0.000 description 6
239000007858 starting material Substances 0.000 description 6
238000003756 stirring Methods 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
238000009835 boiling Methods 0.000 description 5
238000001816 cooling Methods 0.000 description 5
229910052943 magnesium sulfate Inorganic materials 0.000 description 5
235000019341 magnesium sulphate Nutrition 0.000 description 5
239000012071 phase Substances 0.000 description 5
239000000047 product Substances 0.000 description 5
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 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
239000000460 chlorine Substances 0.000 description 4
VEAFIFPWFKGVSS-UHFFFAOYSA-N ethyl 3-[2-chloro-2-(4-chlorophenyl)ethenyl]-2,2-dimethylcyclopropane-1-carboxylate Chemical compound CC1(C)C(C(=O)OCC)C1C=C(Cl)C1=CC=C(Cl)C=C1 VEAFIFPWFKGVSS-UHFFFAOYSA-N 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
150000003254 radicals Chemical class 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
239000011734 sodium Substances 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical group [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
YLVXPXINUWURSG-UHFFFAOYSA-N [hydroxy(phenyl)methyl]phosphonic acid Chemical class OP(=O)(O)C(O)C1=CC=CC=C1 YLVXPXINUWURSG-UHFFFAOYSA-N 0.000 description 3
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical class OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 3
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000012312 sodium hydride Substances 0.000 description 3
229910000104 sodium hydride Inorganic materials 0.000 description 3
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
VGUWZCUCNQXGBU-UHFFFAOYSA-N 3-[(4-methylpiperazin-1-yl)methyl]-5-nitro-1h-indole Chemical compound C1CN(C)CCN1CC1=CNC2=CC=C([N+]([O-])=O)C=C12 VGUWZCUCNQXGBU-UHFFFAOYSA-N 0.000 description 2
AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
235000010290 biphenyl Nutrition 0.000 description 2
239000004305 biphenyl Substances 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
LXCYSACZTOKNNS-UHFFFAOYSA-N diethoxy(oxo)phosphanium Chemical compound CCO[P+](=O)OCC LXCYSACZTOKNNS-UHFFFAOYSA-N 0.000 description 2
238000004821 distillation Methods 0.000 description 2
ZFZXRNVTYVRULM-NKWVEPMBSA-N ethyl (1s,3s)-3-formyl-2,2-dimethylcyclopropane-1-carboxylate Chemical compound CCOC(=O)[C@H]1[C@H](C=O)C1(C)C ZFZXRNVTYVRULM-NKWVEPMBSA-N 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
239000003502 gasoline Substances 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
150000002431 hydrogen Chemical class 0.000 description 2
239000002917 insecticide Substances 0.000 description 2
239000000155 melt Substances 0.000 description 2
KVSRWNPBUMDYOQ-UHFFFAOYSA-N methyl 3-formyl-2,2-dimethylcyclopropane-1-carboxylate Chemical compound COC(=O)C1C(C=O)C1(C)C KVSRWNPBUMDYOQ-UHFFFAOYSA-N 0.000 description 2
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 2
FXLOVSHXALFLKQ-UHFFFAOYSA-N p-tolualdehyde Chemical compound CC1=CC=C(C=O)C=C1 FXLOVSHXALFLKQ-UHFFFAOYSA-N 0.000 description 2
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
239000007787 solid Substances 0.000 description 2
RIQJHXWKWXDLFM-UHFFFAOYSA-N (4-chlorophenyl)-diethoxyphosphorylmethanol Chemical compound CCOP(=O)(OCC)C(O)C1=CC=C(Cl)C=C1 RIQJHXWKWXDLFM-UHFFFAOYSA-N 0.000 description 1
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
BFNMOMYTTGHNGJ-UHFFFAOYSA-N 2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1(C)CC1C(O)=O BFNMOMYTTGHNGJ-UHFFFAOYSA-N 0.000 description 1
WEXGRJPJMNUCMG-UHFFFAOYSA-N 2-diethoxyphosphorylethylbenzene Chemical compound CCOP(=O)(OCC)CCC1=CC=CC=C1 WEXGRJPJMNUCMG-UHFFFAOYSA-N 0.000 description 1
239000001431 2-methylbenzaldehyde Substances 0.000 description 1
SDTMFDGELKWGFT-UHFFFAOYSA-N 2-methylpropan-2-olate Chemical compound CC(C)(C)[O-] SDTMFDGELKWGFT-UHFFFAOYSA-N 0.000 description 1
OLKWYZYVQYPFIM-UHFFFAOYSA-N 3-[2-chloro-2-(4-chlorophenyl)ethenyl]-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound OC(=O)C1C(C)(C)C1C=C(Cl)C1=CC=C(Cl)C=C1 OLKWYZYVQYPFIM-UHFFFAOYSA-N 0.000 description 1
SUISZCALMBHJQX-UHFFFAOYSA-N 3-bromobenzaldehyde Chemical compound BrC1=CC=CC(C=O)=C1 SUISZCALMBHJQX-UHFFFAOYSA-N 0.000 description 1
ZRYZBQLXDKPBDU-UHFFFAOYSA-N 4-bromobenzaldehyde Chemical compound BrC1=CC=C(C=O)C=C1 ZRYZBQLXDKPBDU-UHFFFAOYSA-N 0.000 description 1
UOQXIWFBQSVDPP-UHFFFAOYSA-N 4-fluorobenzaldehyde Chemical compound FC1=CC=C(C=O)C=C1 UOQXIWFBQSVDPP-UHFFFAOYSA-N 0.000 description 1
JLYBFZPYDXMCQA-UHFFFAOYSA-N C1=CC(=CC=C1C(P(=O)(O)O)Cl)Br Chemical compound C1=CC(=CC=C1C(P(=O)(O)O)Cl)Br JLYBFZPYDXMCQA-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
241000700159 Rattus Species 0.000 description 1
206010052428 Wound Diseases 0.000 description 1
208000027418 Wounds and injury Diseases 0.000 description 1
PRYADGLPOUGSHK-UHFFFAOYSA-N [(3,4-dichlorophenyl)-hydroxymethyl]phosphonic acid Chemical compound OP(=O)(O)C(O)C1=CC=C(Cl)C(Cl)=C1 PRYADGLPOUGSHK-UHFFFAOYSA-N 0.000 description 1
OXGYAKFBDNCPJU-UHFFFAOYSA-N [(4-bromophenyl)-hydroxymethyl]phosphonic acid Chemical compound OP(=O)(O)C(O)C1=CC=C(Br)C=C1 OXGYAKFBDNCPJU-UHFFFAOYSA-N 0.000 description 1
HPPXSNUAVNMIES-UHFFFAOYSA-N [(4-chlorophenyl)-hydroxymethyl]phosphonic acid Chemical compound OP(=O)(O)C(O)C1=CC=C(Cl)C=C1 HPPXSNUAVNMIES-UHFFFAOYSA-N 0.000 description 1
VLRPZRWXRRJAED-UHFFFAOYSA-N [(4-fluorophenyl)-hydroxymethyl]phosphonic acid Chemical compound OP(=O)(O)C(O)C1=CC=C(F)C=C1 VLRPZRWXRRJAED-UHFFFAOYSA-N 0.000 description 1
BKGSGRJHDGEZBY-UHFFFAOYSA-N [chloro(dimethoxyphosphoryl)methyl]benzene Chemical compound COP(=O)(OC)C(Cl)C1=CC=CC=C1 BKGSGRJHDGEZBY-UHFFFAOYSA-N 0.000 description 1
QSLFTINMQSKUDB-UHFFFAOYSA-N [chloro-(3,4-dichlorophenyl)methyl]phosphonic acid Chemical compound OP(O)(=O)C(Cl)C1=CC=C(Cl)C(Cl)=C1 QSLFTINMQSKUDB-UHFFFAOYSA-N 0.000 description 1
OZUZLDCSZLULTR-UHFFFAOYSA-N [chloro-(4-chlorophenyl)methyl]phosphonic acid Chemical compound OP(O)(=O)C(Cl)C1=CC=C(Cl)C=C1 OZUZLDCSZLULTR-UHFFFAOYSA-N 0.000 description 1
LPBDPICNFVUQTI-UHFFFAOYSA-N [chloro-(4-fluorophenyl)methyl]phosphonic acid Chemical compound OP(O)(=O)C(Cl)C1=CC=C(F)C=C1 LPBDPICNFVUQTI-UHFFFAOYSA-N 0.000 description 1
OBJGBVJJPHMRGV-UHFFFAOYSA-N [chloro-(4-methylphenyl)methyl]phosphonic acid Chemical compound CC1=CC=C(C(Cl)P(O)(O)=O)C=C1 OBJGBVJJPHMRGV-UHFFFAOYSA-N 0.000 description 1
AFOAUCXHAIELNA-UHFFFAOYSA-N [hydroxy-(4-methylphenyl)methyl]phosphonic acid Chemical compound CC1=CC=C(C(O)P(O)(O)=O)C=C1 AFOAUCXHAIELNA-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
150000004703 alkoxides Chemical class 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
238000012512 characterization method Methods 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
239000012320 chlorinating reagent Substances 0.000 description 1
238000013375 chromatographic separation Methods 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
SULWMEGSVQCTSK-UHFFFAOYSA-N diethyl hydrogen phosphite Chemical compound CCOP(O)OCC SULWMEGSVQCTSK-UHFFFAOYSA-N 0.000 description 1
DLQDGVZAEYZNTG-UHFFFAOYSA-N dimethyl hydrogen phosphite Chemical compound COP(O)OC DLQDGVZAEYZNTG-UHFFFAOYSA-N 0.000 description 1
CZHYKKAKFWLGJO-UHFFFAOYSA-N dimethyl phosphite Chemical compound COP([O-])OC CZHYKKAKFWLGJO-UHFFFAOYSA-N 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 1
TXSLRJKVDMLCFN-UHFFFAOYSA-N ethyl 3-(2-chloro-2-phenylethenyl)-2,2-dimethylcyclopropane-1-carboxylate Chemical compound CC1(C)C(C(=O)OCC)C1C=C(Cl)C1=CC=CC=C1 TXSLRJKVDMLCFN-UHFFFAOYSA-N 0.000 description 1
ZFZXRNVTYVRULM-UHFFFAOYSA-N ethyl 3-formyl-2,2-dimethylcyclopropane-1-carboxylate Chemical compound CCOC(=O)C1C(C=O)C1(C)C ZFZXRNVTYVRULM-UHFFFAOYSA-N 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
239000005457 ice water Substances 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
150000002642 lithium compounds Chemical class 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
CDXVUROVRIFQMV-UHFFFAOYSA-N oxo(diphenoxy)phosphanium Chemical compound C=1C=CC=CC=1O[P+](=O)OC1=CC=CC=C1 CDXVUROVRIFQMV-UHFFFAOYSA-N 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
ZUPDNLCLXSWMAE-UHFFFAOYSA-N potassium;butan-2-olate Chemical compound [K+].CCC(C)[O-] ZUPDNLCLXSWMAE-UHFFFAOYSA-N 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
OGHBATFHNDZKSO-UHFFFAOYSA-N propan-2-olate Chemical compound CC(C)[O-] OGHBATFHNDZKSO-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
239000013557 residual solvent Substances 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000001308 synthesis method Methods 0.000 description 1
JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
LGQXXHMEBUOXRP-UHFFFAOYSA-N tributyl borate Chemical compound CCCCOB(OCCCC)OCCCC LGQXXHMEBUOXRP-UHFFFAOYSA-N 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4056—Esters of arylalkanephosphonic acids
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C61/16—Unsaturated compounds
- C07C61/40—Unsaturated compounds containing halogen

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Health & Medical Sciences (AREA)
Pest Control & Pesticides (AREA)
Molecular Biology (AREA)
Agronomy & Crop Science (AREA)
Biochemistry (AREA)
Plant Pathology (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

CS794247A 1978-06-21 1979-06-20 Method of making the derivatives of the clorstyrylpropan carboxyl acid CS207797B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19782827101 DE2827101A1 (de)	1978-06-21	1978-06-21	Verfahren zur herstellung von chloro-styryl-cyclopropan-carbonsaeure- derivaten

Publications (1)

Publication Number	Publication Date
CS207797B2 true CS207797B2 (en)	1981-08-31

Family

ID=6042299

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS794247A CS207797B2 (en)	1978-06-21	1979-06-20	Method of making the derivatives of the clorstyrylpropan carboxyl acid

Country Status (8)

Country	Link
EP (1)	EP0006205B1 (da)
JP (1)	JPS552685A (da)
BR (1)	BR7903897A (da)
CS (1)	CS207797B2 (da)
DE (2)	DE2827101A1 (da)
DK (1)	DK257779A (da)
HU (1)	HU175701B (da)
IL (1)	IL57591A0 (da)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2916358A1 (de)	1979-04-23	1980-11-06	Bayer Ag	Substituierte styrylcyclopropancarbonsaeureester, verfahren zu ihrer herstellung sowie ihre verwendung als insektizide und akarizide
DE2916375A1 (de) *	1979-04-23	1980-11-06	Bayer Ag	Verfahren zur herstellung von styryl-cyclopropan-carbonsaeureestern und neue zwischenprodukte dafuer
DE2916401A1 (de) *	1979-04-23	1980-11-06	Bayer Ag	Verfahren zur herstellung von 3-(2-arylvinyl)-2,2-dimethyl-cyclopropan-1-carbon- saeureestern und neue zwischenprodukte dafuer
DE2916417A1 (de) *	1979-04-23	1980-11-06	Bayer Ag	Verfahren zur herstellung von 3-(aryl- vinyl)-2,2-dimethyl-cyclopropan-1-carbonsaeureestern und neue zwischenprodukte dafuer
DE2916357A1 (de) *	1979-04-23	1980-11-06	Bayer Ag	Verfahren zur herstellung von 3-(2-aryl-vinyl)-2,2-dimethyl-cyclopropan-1-carbonsaeureestern und neue zwischenprodukte dafuer
DE2916321A1 (de) *	1979-04-23	1980-11-06	Bayer Ag	Verfahren zur herstellung von styryl- cyclopropan-carbonsaeureestern und neue zwischenprodukte dafuer
DE2929645A1 (de)	1979-07-21	1981-02-12	Bayer Ag	Verfahren zur herstellung von 1,1- dichloralkenen
US4296241A (en) *	1979-07-21	1981-10-20	Bayer Aktiengesellschaft	Preparation of 3-(2,2-dichlorovinyl)-2,2-dimethyl-cyclopropane-1-carboxylic acid derivatives
DE3000065A1 (de) *	1980-01-03	1981-07-09	Bayer Ag, 5090 Leverkusen	Verfahren zur herstellung von halogenalkenen
DE3035149A1 (de) *	1980-09-18	1982-04-22	Bayer Ag, 5090 Leverkusen	Verfahren zur herstellung von trans-3-(z-2-chlor-2-aryl-vinyl)-2,2-dimethylcyclopropan-1-carbonsaeure-derivaten, neue zwischenprodukte hierfuer, verfahren zu deren herstellung und verwendung von zwischenprodukten in schaedlingsbekaempfungsmitteln

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA1260486A (en) *	1976-08-27	1989-09-26	John F. Engel	Insecticidal styryl- and substituted- styrylcyclopropanecarboxylates

1978
- 1978-06-21 DE DE19782827101 patent/DE2827101A1/de not_active Withdrawn
1979
- 1979-06-11 DE DE7979101864T patent/DE2963721D1/de not_active Expired
- 1979-06-11 EP EP79101864A patent/EP0006205B1/de not_active Expired
- 1979-06-18 IL IL57591A patent/IL57591A0/xx unknown
- 1979-06-19 JP JP7639079A patent/JPS552685A/ja active Pending
- 1979-06-20 DK DK257779A patent/DK257779A/da not_active Application Discontinuation
- 1979-06-20 BR BR7903897A patent/BR7903897A/pt unknown
- 1979-06-20 CS CS794247A patent/CS207797B2/cs unknown
- 1979-06-21 HU HU79BA3796A patent/HU175701B/hu unknown

Also Published As

Publication number	Publication date
DE2827101A1 (de)	1980-01-10
EP0006205A1 (de)	1980-01-09
DK257779A (da)	1979-12-22
EP0006205B1 (de)	1982-09-22
HU175701B (hu)	1980-10-28
IL57591A0 (en)	1979-10-31
DE2963721D1 (en)	1982-11-04
BR7903897A (pt)	1980-03-04
JPS552685A (en)	1980-01-10

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HU188495B (en)	1986-04-28	Process for preparing derivatives of bromo-stiryl-cyclopropane-carboxylic acid
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US4424166A (en)	1984-01-03	Preparation of 1,1-dihalogeno-alkenes
EP0019719A1 (de)	1980-12-10	Verfahren zur Herstellung von Alkenen, neue Zwischenprodukte zu ihrer Herstellung und Verfahren zu deren Herstellung
CA2083653A1 (en)	1993-06-22	Preparation of alkenols
FI64571B (fi)	1983-08-31	Foerfarande foer framstaellning av 2-aryl-propionsyra
HU182691B (en)	1984-02-28	Process for preparing 3-/2,2-dichloro-vinyl/-2,2-dimethyl-cyclopropane-carboxylic acid and esters thereof
CS212349B2 (en)	1982-03-26	Method of making the esters of the 3-/2-arylvinyl/-2,2- dimethyl-cyclopropan-1-carboxyl acids