DD152539A5 - Verfahren zur herstellung von phenylalkansaeuren - Google Patents
Verfahren zur herstellung von phenylalkansaeuren Download PDFInfo
- Publication number
- DD152539A5 DD152539A5 DD79220007A DD22000779A DD152539A5 DD 152539 A5 DD152539 A5 DD 152539A5 DD 79220007 A DD79220007 A DD 79220007A DD 22000779 A DD22000779 A DD 22000779A DD 152539 A5 DD152539 A5 DD 152539A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- alpha
- isopropyl
- acid
- preparation
- phenoxybenzyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 29
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 title 1
- 238000002360 preparation method Methods 0.000 claims abstract description 37
- 239000002253 acid Substances 0.000 claims abstract description 27
- 150000001875 compounds Chemical class 0.000 claims abstract description 10
- 150000007513 acids Chemical class 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 20
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract description 18
- -1 m-phenoxybenzyl esters Chemical class 0.000 abstract description 15
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract description 12
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract description 6
- 239000002904 solvent Substances 0.000 abstract description 6
- 238000001704 evaporation Methods 0.000 abstract description 5
- 230000008020 evaporation Effects 0.000 abstract description 5
- 230000000749 insecticidal effect Effects 0.000 abstract description 5
- 239000003795 chemical substances by application Substances 0.000 abstract description 4
- QIMUYXGVXHABQI-UHFFFAOYSA-N 3-methyl-2-[4-(trifluoromethoxy)phenyl]butanoic acid Chemical compound CC(C)C(C(O)=O)C1=CC=C(OC(F)(F)F)C=C1 QIMUYXGVXHABQI-UHFFFAOYSA-N 0.000 abstract description 3
- KPZFKIYGSAJNLQ-UHFFFAOYSA-N 3-methyl-2-[4-(trifluoromethoxy)phenyl]butanoyl chloride Chemical compound CC(C)C(C(Cl)=O)C1=CC=C(OC(F)(F)F)C=C1 KPZFKIYGSAJNLQ-UHFFFAOYSA-N 0.000 abstract description 3
- 230000000895 acaricidal effect Effects 0.000 abstract description 3
- 238000009835 boiling Methods 0.000 abstract description 3
- 239000000543 intermediate Substances 0.000 abstract description 3
- 238000010992 reflux Methods 0.000 abstract description 3
- GXUQMKBQDGPMKZ-UHFFFAOYSA-N 2-hydroxy-2-(3-phenoxyphenyl)acetonitrile Chemical compound N#CC(O)C1=CC=CC(OC=2C=CC=CC=2)=C1 GXUQMKBQDGPMKZ-UHFFFAOYSA-N 0.000 abstract description 2
- PYQWVKPCMUFCRW-UHFFFAOYSA-N [cyano-(3-phenoxyphenyl)methyl] 3-methyl-2-[4-(trifluoromethoxy)phenyl]butanoate Chemical compound C=1C=C(OC(F)(F)F)C=CC=1C(C(C)C)C(=O)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 PYQWVKPCMUFCRW-UHFFFAOYSA-N 0.000 abstract description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- 239000000047 product Substances 0.000 description 21
- 239000000460 chlorine Substances 0.000 description 16
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 239000003921 oil Substances 0.000 description 12
- 235000019198 oils Nutrition 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 238000004458 analytical method Methods 0.000 description 8
- 239000007787 solid Substances 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- GDBITPXOESTAML-UHFFFAOYSA-N 2-(4-hydroxyphenyl)-3-methylbutyric acid Chemical compound CC(C)C(C(O)=O)C1=CC=C(O)C=C1 GDBITPXOESTAML-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- RQCIDSUZSLVZLL-UHFFFAOYSA-N 2-(3-chloro-4-hydroxyphenyl)-3-methylbutanoic acid Chemical compound CC(C)C(C(O)=O)C1=CC=C(O)C(Cl)=C1 RQCIDSUZSLVZLL-UHFFFAOYSA-N 0.000 description 3
- ZAICCCIGPJFMHN-UHFFFAOYSA-N 2-[3-bromo-4-(difluoromethoxy)phenyl]-3-methylbutanoic acid Chemical compound CC(C)C(C(O)=O)C1=CC=C(OC(F)F)C(Br)=C1 ZAICCCIGPJFMHN-UHFFFAOYSA-N 0.000 description 3
- 241000238876 Acari Species 0.000 description 3
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 description 3
- 241000238631 Hexapoda Species 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- KXZUCTJCCFYZKF-UHFFFAOYSA-N 2-(3-bromo-4-hydroxyphenyl)-3-methylbutanoic acid Chemical compound CC(C)C(C(O)=O)C1=CC=C(O)C(Br)=C1 KXZUCTJCCFYZKF-UHFFFAOYSA-N 0.000 description 2
- OFCMGCZEFVKTAN-UHFFFAOYSA-N 2-(3-fluoro-4-methoxyphenyl)acetonitrile Chemical compound COC1=CC=C(CC#N)C=C1F OFCMGCZEFVKTAN-UHFFFAOYSA-N 0.000 description 2
- FXFAEPDUBWMUHY-UHFFFAOYSA-N 2-(4-hydroxy-3-nitrophenyl)-3-methylbutanoic acid Chemical compound CC(C)C(C(O)=O)C1=CC=C(O)C([N+]([O-])=O)=C1 FXFAEPDUBWMUHY-UHFFFAOYSA-N 0.000 description 2
- FEVVTKCAZXCXEQ-UHFFFAOYSA-N 2-(4-hydroxyphenyl)pentanoic acid Chemical compound CCCC(C(O)=O)C1=CC=C(O)C=C1 FEVVTKCAZXCXEQ-UHFFFAOYSA-N 0.000 description 2
- LFESTEOQWFVSNE-UHFFFAOYSA-N 2-[4-(difluoromethoxy)-3-fluorophenyl]-3-methylbutanoic acid Chemical compound CC(C)C(C(O)=O)C1=CC=C(OC(F)F)C(F)=C1 LFESTEOQWFVSNE-UHFFFAOYSA-N 0.000 description 2
- ZRYXMBWYACLLRH-UHFFFAOYSA-N 2-[4-(difluoromethoxy)phenyl]-3-methylbutanoic acid Chemical compound CC(C)C(C(O)=O)C1=CC=C(OC(F)F)C=C1 ZRYXMBWYACLLRH-UHFFFAOYSA-N 0.000 description 2
- SJTBRFHBXDZMPS-UHFFFAOYSA-N 3-fluorophenol Chemical compound OC1=CC=CC(F)=C1 SJTBRFHBXDZMPS-UHFFFAOYSA-N 0.000 description 2
- XQXPVVBIMDBYFF-UHFFFAOYSA-N 4-hydroxyphenylacetic acid Chemical compound OC(=O)CC1=CC=C(O)C=C1 XQXPVVBIMDBYFF-UHFFFAOYSA-N 0.000 description 2
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- KGANAERDZBAECK-UHFFFAOYSA-N (3-phenoxyphenyl)methanol Chemical compound OCC1=CC=CC(OC=2C=CC=CC=2)=C1 KGANAERDZBAECK-UHFFFAOYSA-N 0.000 description 1
- FRHAFNRTNWOQIL-UHFFFAOYSA-N (3-phenoxyphenyl)methyl 3-methyl-2-[4-(trifluoromethoxy)phenyl]butanoate Chemical compound C=1C=C(OC(F)(F)F)C=CC=1C(C(C)C)C(=O)OCC(C=1)=CC=CC=1OC1=CC=CC=C1 FRHAFNRTNWOQIL-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- DIXHCBLMPWFTAF-UHFFFAOYSA-N 2-(3,5-dichloro-4-hydroxyphenyl)-3-methylbutanoic acid Chemical compound CC(C)C(C(O)=O)C1=CC(Cl)=C(O)C(Cl)=C1 DIXHCBLMPWFTAF-UHFFFAOYSA-N 0.000 description 1
- VTHVFMTYTRKDIH-UHFFFAOYSA-N 2-(3-fluoro-4-methoxyphenyl)-3-methylbutanenitrile Chemical compound COC1=CC=C(C(C#N)C(C)C)C=C1F VTHVFMTYTRKDIH-UHFFFAOYSA-N 0.000 description 1
- WWDKRALQLRWOBN-UHFFFAOYSA-N 2-(4-hydroxy-3-methylphenyl)-3-methylbutanoic acid Chemical compound CC(C)C(C(O)=O)C1=CC=C(O)C(C)=C1 WWDKRALQLRWOBN-UHFFFAOYSA-N 0.000 description 1
- GEQWCUVIQMRCAZ-UHFFFAOYSA-N 2-(4-hydroxyphenyl)butanoic acid Chemical compound CCC(C(O)=O)C1=CC=C(O)C=C1 GEQWCUVIQMRCAZ-UHFFFAOYSA-N 0.000 description 1
- QOMACJMHUFTRJI-UHFFFAOYSA-N 2-(4-methoxy-3-methylphenyl)acetonitrile Chemical compound COC1=CC=C(CC#N)C=C1C QOMACJMHUFTRJI-UHFFFAOYSA-N 0.000 description 1
- CNBUXJALZYSKQJ-UHFFFAOYSA-N 2-(4-methoxyphenyl)-3-methylbutanenitrile Chemical compound COC1=CC=C(C(C#N)C(C)C)C=C1 CNBUXJALZYSKQJ-UHFFFAOYSA-N 0.000 description 1
- FKHHHAOUKWMETF-UHFFFAOYSA-N 2-(4-methoxyphenyl)butanenitrile Chemical compound CCC(C#N)C1=CC=C(OC)C=C1 FKHHHAOUKWMETF-UHFFFAOYSA-N 0.000 description 1
- QYEXJHNAPHRQOD-UHFFFAOYSA-N 2-(4-methoxyphenyl)pentanenitrile Chemical compound CCCC(C#N)C1=CC=C(OC)C=C1 QYEXJHNAPHRQOD-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- QDOASINGNSAKBO-UHFFFAOYSA-N 2-[3,5-dichloro-4-(difluoromethoxy)phenyl]-3-methylbutanoic acid Chemical compound CC(C)C(C(O)=O)C1=CC(Cl)=C(OC(F)F)C(Cl)=C1 QDOASINGNSAKBO-UHFFFAOYSA-N 0.000 description 1
- IXCJBVMHAFUXBB-UHFFFAOYSA-N 2-[4-(difluoromethoxy)-3-methoxyphenyl]-3-methylbutanoic acid Chemical compound COC1=CC(C(C(C)C)C(O)=O)=CC=C1OC(F)F IXCJBVMHAFUXBB-UHFFFAOYSA-N 0.000 description 1
- LXJRCJQNKRXQLY-UHFFFAOYSA-N 2-[4-(difluoromethoxy)phenyl]pentanoic acid Chemical compound CCCC(C(O)=O)C1=CC=C(OC(F)F)C=C1 LXJRCJQNKRXQLY-UHFFFAOYSA-N 0.000 description 1
- NAMYKGVDVNBCFQ-UHFFFAOYSA-N 2-bromopropane Chemical compound CC(C)Br NAMYKGVDVNBCFQ-UHFFFAOYSA-N 0.000 description 1
- NLGIGFKKNPDYQL-UHFFFAOYSA-N 3-(3-fluorophenoxy)benzaldehyde Chemical compound FC1=CC=CC(OC=2C=C(C=O)C=CC=2)=C1 NLGIGFKKNPDYQL-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
- SUISZCALMBHJQX-UHFFFAOYSA-N 3-bromobenzaldehyde Chemical compound BrC1=CC=CC(C=O)=C1 SUISZCALMBHJQX-UHFFFAOYSA-N 0.000 description 1
- 101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- FEVUSIUXCXICPJ-UHFFFAOYSA-N CC(C)C(C#N)(C1=CC=C(C(C1CC2=CC=CC=C2)(OC3=CC=CC=C3)F)OC(F)F)C(=O)O Chemical compound CC(C)C(C#N)(C1=CC=C(C(C1CC2=CC=CC=C2)(OC3=CC=CC=C3)F)OC(F)F)C(=O)O FEVUSIUXCXICPJ-UHFFFAOYSA-N 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 125000005997 bromomethyl group Chemical group 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 108700041286 delta Proteins 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 1
- 229940093499 ethyl acetate Drugs 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- QJHVXBUKLYONEA-UHFFFAOYSA-N methyl 2-[4-(difluoromethoxy)phenyl]acetate Chemical compound COC(=O)CC1=CC=C(OC(F)F)C=C1 QJHVXBUKLYONEA-UHFFFAOYSA-N 0.000 description 1
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- DIAIBWNEUYXDNL-UHFFFAOYSA-N n,n-dihexylhexan-1-amine Chemical compound CCCCCCN(CCCCCC)CCCCCC DIAIBWNEUYXDNL-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
- 239000003279 phenylacetic acid Substances 0.000 description 1
- LUMVCLJFHCTMCV-UHFFFAOYSA-M potassium;hydroxide;hydrate Chemical compound O.[OH-].[K+] LUMVCLJFHCTMCV-UHFFFAOYSA-M 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/10—Aromatic or araliphatic carboxylic acids, or thio analogues thereof; Derivatives thereof
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/34—Nitriles
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
- A01N37/38—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
-
- 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
- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
- A01N41/10—Sulfones; Sulfoxides
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
- C07C255/38—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by esterified hydroxy 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
- C07C47/575—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/08—Preparation of carboxylic acids or their salts, halides or anhydrides from nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/363—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/367—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in singly bound form
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
- C07C51/60—Preparation of carboxylic acid halides by conversion of carboxylic acids or their anhydrides or esters, lactones, salts into halides with the same carboxylic acid part
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/612—Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a six-membered aromatic ring in the acid moiety
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/612—Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a six-membered aromatic ring in the acid moiety
- C07C69/614—Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a six-membered aromatic ring in the acid moiety of phenylacetic acid
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Environmental Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Tropical Medicine & Parasitology (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US05/890,568 US4199595A (en) | 1976-10-01 | 1978-03-20 | M-phenoxybenzyl and α-cyano-M-phenoxybenzyl esters of 2-haloalkyl (oxy-, thio-, sulfinyl-, or sulfonyl)phenylalkanoic acids |
US05/890,721 US4178460A (en) | 1976-10-01 | 1978-03-20 | 2-Haloalkyl(oxy-, thio-, sulfinyl-, or sulfonyl)-phenylalkanoic acids |
Publications (1)
Publication Number | Publication Date |
---|---|
DD152539A5 true DD152539A5 (de) | 1981-12-02 |
Family
ID=27128953
Family Applications (5)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DD79220007A DD152539A5 (de) | 1978-03-20 | 1979-03-20 | Verfahren zur herstellung von phenylalkansaeuren |
DD79211694A DD150455A6 (de) | 1978-03-20 | 1979-03-20 | Verfahren zur herstellung von phenylalkansaeure-m-phenoxy-benzylestern |
DD79219673A DD149601A6 (de) | 1978-03-20 | 1979-03-20 | Verfahren zur bekaempfung von insekten und milben |
DD79220465A DD154535A5 (de) | 1978-03-20 | 1979-03-20 | Verfahren zur herstellung von (+)-alpha-isopropyl-4-di-oder-trifluormethoxyphenylessigsaeure |
DD79211693A DD143601A5 (de) | 1978-03-20 | 1979-03-20 | Verfahren zur herstellung von phenylalkansaeure-m-phenoxybenzylestern |
Family Applications After (4)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DD79211694A DD150455A6 (de) | 1978-03-20 | 1979-03-20 | Verfahren zur herstellung von phenylalkansaeure-m-phenoxy-benzylestern |
DD79219673A DD149601A6 (de) | 1978-03-20 | 1979-03-20 | Verfahren zur bekaempfung von insekten und milben |
DD79220465A DD154535A5 (de) | 1978-03-20 | 1979-03-20 | Verfahren zur herstellung von (+)-alpha-isopropyl-4-di-oder-trifluormethoxyphenylessigsaeure |
DD79211693A DD143601A5 (de) | 1978-03-20 | 1979-03-20 | Verfahren zur herstellung von phenylalkansaeure-m-phenoxybenzylestern |
Country Status (17)
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2837524A1 (de) * | 1978-08-28 | 1980-03-20 | Bayer Ag | Substituierte alpha-phenyl-carbonsaeure- (4-fluoro-3-phenoxy-benzyl)-ester, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide |
IL61348A (en) * | 1979-11-28 | 1984-05-31 | American Cyanamid Co | (-)-alpha-cyano-m-phenoxybenzyl(+)alpha-isopropyl-4-difluoromethoxy-phenylacetate,its preparation and its use as an insecticide |
JPS56133253A (en) * | 1980-03-24 | 1981-10-19 | Sumitomo Chem Co Ltd | Optical isomer of cyanohydrin ester, its production and insecticide and acaricide containing the same as effective ingredient |
JPS56139445A (en) * | 1980-04-02 | 1981-10-30 | Sumitomo Chem Co Ltd | Stereoisomer of cyanohydrin ester, its production and insecticide, acaricide containing the same as active principle |
JPS5793948A (en) * | 1980-12-02 | 1982-06-11 | Sumitomo Chem Co Ltd | Preparation of stereoisomer mixture of higher active phenylacetic ester derivative |
DE3103325A1 (de) * | 1981-01-31 | 1982-08-26 | Bayer Ag, 5090 Leverkusen | 4-fluor-3-halophenoxy-benzylester, verfahren zu deren herstellung und deren verwendung in schaedlingsbekaempfungsmitteln sowie neue zwischenprodukte und verfahren zu deren herstellung |
FR2512815B1 (fr) * | 1981-04-16 | 1989-04-14 | Roussel Uclaf | Nouveaux derives de l'acide cyclopropane carboxylique, leur procede de preparation, leur application a la lutte contre les parasites |
IL69304A0 (en) * | 1982-08-23 | 1983-11-30 | American Cyanamid Co | Method for the preparation of difluoromethoxyaromatic compounds |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5133612B2 (enrdf_load_stackoverflow) * | 1973-04-19 | 1976-09-21 | Sumitomo Chemical Co | |
IL52973A (en) * | 1976-10-01 | 1983-10-31 | American Cyanamid Co | Alpha-(haloalkoxy and haloalkyl-thiophenyl)alkanoic acid ester derivatives,their preparation and insecticidal and acaricidal compositions containing them |
-
1979
- 1979-02-16 GR GR58388A patent/GR74446B/el unknown
- 1979-03-15 NZ NZ189915A patent/NZ189915A/xx unknown
- 1979-03-17 RO RO7996953A patent/RO79551A/ro unknown
- 1979-03-19 DK DK112679A patent/DK112679A/da not_active Application Discontinuation
- 1979-03-19 AU AU45251/79A patent/AU528525B2/en not_active Expired
- 1979-03-19 BR BR7901697A patent/BR7901697A/pt unknown
- 1979-03-19 AU AU45242/79A patent/AU525146B2/en not_active Ceased
- 1979-03-19 NL NL7902153A patent/NL7902153A/xx not_active Application Discontinuation
- 1979-03-19 CH CH257379A patent/CH641638A5/de not_active IP Right Cessation
- 1979-03-19 GB GB7909542A patent/GB2017688B/en not_active Expired
- 1979-03-19 AT AT0204979A patent/AT367965B/de not_active IP Right Cessation
- 1979-03-19 PL PL1979214234A patent/PL123011B1/pl unknown
- 1979-03-19 CH CH257479A patent/CH640513A5/de not_active IP Right Cessation
- 1979-03-19 SE SE7902467A patent/SE444313B/sv not_active IP Right Cessation
- 1979-03-20 AR AR275883A patent/AR228014A1/es active
- 1979-03-20 HU HU79AE565A patent/HU182016B/hu unknown
- 1979-03-20 ES ES1979478785A patent/ES478785A0/es active Granted
- 1979-03-20 DD DD79220007A patent/DD152539A5/de unknown
- 1979-03-20 JP JP3318979A patent/JPS54135742A/ja active Granted
- 1979-03-20 ES ES478787A patent/ES478787A0/es active Granted
- 1979-03-20 DD DD79211694A patent/DD150455A6/de not_active IP Right Cessation
- 1979-03-20 DD DD79219673A patent/DD149601A6/de unknown
- 1979-03-20 DD DD79220465A patent/DD154535A5/de unknown
- 1979-03-20 DD DD79211693A patent/DD143601A5/de unknown
Also Published As
Publication number | Publication date |
---|---|
GB2017688A (en) | 1979-10-10 |
HU182016B (en) | 1983-12-28 |
AT367965B (de) | 1982-08-25 |
PL123011B1 (en) | 1982-09-30 |
RO79551A (ro) | 1982-08-17 |
CH641638A5 (de) | 1984-03-15 |
JPS54135742A (en) | 1979-10-22 |
AU525146B2 (en) | 1982-10-21 |
BR7901697A (pt) | 1979-10-16 |
ES8303283A2 (es) | 1983-02-01 |
SE7902467L (enrdf_load_stackoverflow) | 1979-11-19 |
AU4525179A (en) | 1979-09-27 |
PL214234A3 (enrdf_load_stackoverflow) | 1980-08-25 |
SE444313B (sv) | 1986-04-07 |
ATA204979A (de) | 1982-01-15 |
DD149601A6 (de) | 1981-07-22 |
GB2017688B (en) | 1982-08-18 |
AU528525B2 (en) | 1983-05-05 |
AR228014A1 (es) | 1983-01-14 |
DK112679A (da) | 1979-09-21 |
DD143601A5 (de) | 1980-09-03 |
NL7902153A (nl) | 1979-09-24 |
GR74446B (enrdf_load_stackoverflow) | 1984-06-28 |
ES8105253A1 (es) | 1981-05-16 |
ES478785A0 (es) | 1983-02-01 |
JPS6362507B2 (enrdf_load_stackoverflow) | 1988-12-02 |
AU4524279A (en) | 1979-09-27 |
DD150455A6 (de) | 1981-09-02 |
CH640513A5 (de) | 1984-01-13 |
ES478787A0 (es) | 1981-05-16 |
NZ189915A (en) | 1981-04-24 |
DD154535A5 (de) | 1982-03-31 |
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