NL7907749A - Werkwijze voor het bereiden van een fenoxycarbonzuurderivaat. - Google Patents

Werkwijze voor het bereiden van een fenoxycarbonzuurderivaat. Download PDF

Info

Publication number: NL7907749A
Authority: NL; Netherlands
Prior art keywords: formula; phenol; ethyl; salts; phenoxy
Prior art date: 1978-11-01

Application number

NL7907749A

Other languages

English (en)

Dutch (nl)

Original Assignee

Ihara Chemical Ind Co

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.)

1978-11-01

Filing date

1979-10-22

Publication date

1980-05-06

1979-10-22 Application filed by Ihara Chemical Ind Co filed Critical Ihara Chemical Ind Co

1980-05-06 Publication of NL7907749A publication Critical patent/NL7907749A/nl

Links

238000004519 manufacturing process Methods 0.000 title claims description 5
HHNQGORRSUIOFR-UHFFFAOYSA-N phenoxy hydrogen carbonate Chemical class OC(=O)OOC1=CC=CC=C1 HHNQGORRSUIOFR-UHFFFAOYSA-N 0.000 title 1
-1 phenol compound Chemical class 0.000 claims description 50
238000000034 method Methods 0.000 claims description 18
238000006243 chemical reaction Methods 0.000 claims description 14
QIIPQYDSKRYMFG-UHFFFAOYSA-N phenyl hydrogen carbonate Chemical class OC(=O)OC1=CC=CC=C1 QIIPQYDSKRYMFG-UHFFFAOYSA-N 0.000 claims description 13
150000002366 halogen compounds Chemical class 0.000 claims description 12
125000005843 halogen group Chemical group 0.000 claims description 12
125000000217 alkyl group Chemical group 0.000 claims description 11
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
150000004714 phosphonium salts Chemical group 0.000 claims description 11
150000003242 quaternary ammonium salts Chemical class 0.000 claims description 9
150000003839 salts Chemical class 0.000 claims description 9
239000002904 solvent Substances 0.000 claims description 8
239000002585 base Substances 0.000 claims description 7
125000004093 cyano group Chemical group *C#N 0.000 claims description 7
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
150000001339 alkali metal compounds Chemical class 0.000 claims description 6
150000001341 alkaline earth metal compounds Chemical class 0.000 claims description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
239000012454 non-polar solvent Substances 0.000 claims description 3
125000005497 tetraalkylphosphonium group Chemical group 0.000 claims description 3
150000005621 tetraalkylammonium salts Chemical class 0.000 claims description 2
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 36
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 15
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 13
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
239000000203 mixture Substances 0.000 description 10
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
150000002989 phenols Chemical class 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
FJFSSESWAFPCSU-UHFFFAOYSA-N 4-[4-(trifluoromethyl)phenoxy]phenol Chemical compound C1=CC(O)=CC=C1OC1=CC=C(C(F)(F)F)C=C1 FJFSSESWAFPCSU-UHFFFAOYSA-N 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
150000001875 compounds Chemical class 0.000 description 5
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
229910000027 potassium carbonate Inorganic materials 0.000 description 5
238000003756 stirring Methods 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
JFOMAVKCSFUFND-SNAWJCMRSA-N ethyl (e)-4-bromopent-2-enoate Chemical compound CCOC(=O)\C=C\C(C)Br JFOMAVKCSFUFND-SNAWJCMRSA-N 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
QTNZUCWMRAIYCB-UHFFFAOYSA-M tributyl(ethyl)azanium;bromide Chemical compound [Br-].CCCC[N+](CC)(CCCC)CCCC QTNZUCWMRAIYCB-UHFFFAOYSA-M 0.000 description 4
SXERGJJQSKIUIC-UHFFFAOYSA-N 2-Phenoxypropionic acid Chemical compound OC(=O)C(C)OC1=CC=CC=C1 SXERGJJQSKIUIC-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
239000006227 byproduct Substances 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
238000007086 side reaction Methods 0.000 description 3
HAIUIAZIUDPZIE-UHFFFAOYSA-N 3-bromobutanoic acid Chemical compound CC(Br)CC(O)=O HAIUIAZIUDPZIE-UHFFFAOYSA-N 0.000 description 2
YXXVTDFGMLTZLS-UHFFFAOYSA-N 4-(2-chlorophenoxy)phenol Chemical compound C1=CC(O)=CC=C1OC1=CC=CC=C1Cl YXXVTDFGMLTZLS-UHFFFAOYSA-N 0.000 description 2
GLMSPINECXHASR-UHFFFAOYSA-N 4-(4-chloro-2-nitrophenoxy)phenol Chemical compound C1=CC(O)=CC=C1OC1=CC=C(Cl)C=C1[N+]([O-])=O GLMSPINECXHASR-UHFFFAOYSA-N 0.000 description 2
ZSBDGXGICLIJGD-UHFFFAOYSA-N 4-phenoxyphenol Chemical compound C1=CC(O)=CC=C1OC1=CC=CC=C1 ZSBDGXGICLIJGD-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
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
150000003863 ammonium salts Chemical class 0.000 description 2
CHQVQXZFZHACQQ-UHFFFAOYSA-M benzyl(triethyl)azanium;bromide Chemical compound [Br-].CC[N+](CC)(CC)CC1=CC=CC=C1 CHQVQXZFZHACQQ-UHFFFAOYSA-M 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
BNQRPLGZFADFGA-UHFFFAOYSA-N benzyl(triphenyl)phosphanium Chemical class C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)CC1=CC=CC=C1 BNQRPLGZFADFGA-UHFFFAOYSA-N 0.000 description 2
238000009835 boiling Methods 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
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
229940125898 compound 5 Drugs 0.000 description 2
ARFLASKVLJTEJD-UHFFFAOYSA-N ethyl 2-bromopropanoate Chemical compound CCOC(=O)C(C)Br ARFLASKVLJTEJD-UHFFFAOYSA-N 0.000 description 2
PMRYCMJZYIOIEI-UHFFFAOYSA-N ethyl 4-chloropent-2-enoate Chemical compound CCOC(=O)C=CC(C)Cl PMRYCMJZYIOIEI-UHFFFAOYSA-N 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
229910052753 mercury Inorganic materials 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-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 1
UGRMITBWUVWUEB-UHFFFAOYSA-N 1-$l^{1}-oxidanyl-3-methylbenzene Chemical group CC1=CC=CC([O])=C1 UGRMITBWUVWUEB-UHFFFAOYSA-N 0.000 description 1
CXBDYQVECUFKRK-UHFFFAOYSA-N 1-methoxybutane Chemical compound CCCCOC CXBDYQVECUFKRK-UHFFFAOYSA-N 0.000 description 1
FOIJABNATICWDL-UHFFFAOYSA-N 2-(4-hydroxyphenoxy)-5-(trifluoromethyl)benzonitrile Chemical compound C1=CC(O)=CC=C1OC1=CC=C(C(F)(F)F)C=C1C#N FOIJABNATICWDL-UHFFFAOYSA-N 0.000 description 1
XJNNDKMSXFNMDM-UHFFFAOYSA-N 2-bromopent-2-enoic acid Chemical compound CCC=C(Br)C(O)=O XJNNDKMSXFNMDM-UHFFFAOYSA-N 0.000 description 1
TVSPPYGAFOVROT-UHFFFAOYSA-N 2-phenoxybutanoic acid Chemical compound CCC(C(O)=O)OC1=CC=CC=C1 TVSPPYGAFOVROT-UHFFFAOYSA-N 0.000 description 1
IMUUUWJMMRERBK-UHFFFAOYSA-N 2-phenoxypent-2-enoic acid Chemical compound CCC=C(C(O)=O)OC1=CC=CC=C1 IMUUUWJMMRERBK-UHFFFAOYSA-N 0.000 description 1
LEUUKPQCGDMVCD-UHFFFAOYSA-N 3-bromohexanoic acid Chemical compound CCCC(Br)CC(O)=O LEUUKPQCGDMVCD-UHFFFAOYSA-N 0.000 description 1
IBNHMAVJUSHLBQ-UHFFFAOYSA-N 3-bromopentanoic acid Chemical compound CCC(Br)CC(O)=O IBNHMAVJUSHLBQ-UHFFFAOYSA-N 0.000 description 1
XEEMVPPCXNTVNP-UHFFFAOYSA-N 3-chlorobutanoic acid Chemical compound CC(Cl)CC(O)=O XEEMVPPCXNTVNP-UHFFFAOYSA-N 0.000 description 1
AVXSSSNLOIFJNC-UHFFFAOYSA-N 3-chlorohexanoic acid Chemical compound CCCC(Cl)CC(O)=O AVXSSSNLOIFJNC-UHFFFAOYSA-N 0.000 description 1
OVLLWBPWBDJZIZ-UHFFFAOYSA-N 3-chloropentanoic acid Chemical compound CCC(Cl)CC(O)=O OVLLWBPWBDJZIZ-UHFFFAOYSA-N 0.000 description 1
PEZBINWPXSQPDF-UHFFFAOYSA-N 4-(2,4-dichlorophenoxy)phenol ethyl 2-chloropropanoate Chemical compound ClC(C(=O)OCC)C.ClC1=C(OC2=CC=C(C=C2)O)C=CC(=C1)Cl PEZBINWPXSQPDF-UHFFFAOYSA-N 0.000 description 1
PBLIRIZNKPOKJR-UHFFFAOYSA-N 4-(2,5-dichlorophenoxy)phenol Chemical compound C1=CC(O)=CC=C1OC1=CC(Cl)=CC=C1Cl PBLIRIZNKPOKJR-UHFFFAOYSA-N 0.000 description 1
KUAGGVQYZKIKJW-UHFFFAOYSA-N 4-(3,4-dichlorophenoxy)phenol Chemical compound C1=CC(O)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 KUAGGVQYZKIKJW-UHFFFAOYSA-N 0.000 description 1
SOFDBMTWIADQEP-UHFFFAOYSA-N 4-(3,5-dichlorophenoxy)phenol Chemical compound C1=CC(O)=CC=C1OC1=CC(Cl)=CC(Cl)=C1 SOFDBMTWIADQEP-UHFFFAOYSA-N 0.000 description 1
HMBBTPMHPQGJMR-UHFFFAOYSA-N 4-(4-bromophenoxy)phenol Chemical compound C1=CC(O)=CC=C1OC1=CC=C(Br)C=C1 HMBBTPMHPQGJMR-UHFFFAOYSA-N 0.000 description 1
IAVZWAALTFRVDY-UHFFFAOYSA-N 4-(4-chloro-2-methylphenoxy)phenol Chemical compound CC1=CC(Cl)=CC=C1OC1=CC=C(O)C=C1 IAVZWAALTFRVDY-UHFFFAOYSA-N 0.000 description 1
XQMRZWSYBUCVAX-UHFFFAOYSA-N 4-(4-chlorophenoxy)phenol Chemical compound C1=CC(O)=CC=C1OC1=CC=C(Cl)C=C1 XQMRZWSYBUCVAX-UHFFFAOYSA-N 0.000 description 1
ODZRCMFGWWKUGO-UHFFFAOYSA-N 4-(4-hydroxyphenoxy)-3-nitrobenzonitrile Chemical compound C1=CC(O)=CC=C1OC1=CC=C(C#N)C=C1[N+]([O-])=O ODZRCMFGWWKUGO-UHFFFAOYSA-N 0.000 description 1
SDGFJYRTWKBZFB-UHFFFAOYSA-N 4-(4-methylphenoxy)phenol Chemical compound C1=CC(C)=CC=C1OC1=CC=C(O)C=C1 SDGFJYRTWKBZFB-UHFFFAOYSA-N 0.000 description 1
XLPMQLXJDGDBLH-UHFFFAOYSA-N 4-(4-phenoxyphenoxy)pent-2-enoic acid Chemical compound O(C1=CC=CC=C1)C1=CC=C(OC(C=CC(=O)O)C)C=C1 XLPMQLXJDGDBLH-UHFFFAOYSA-N 0.000 description 1
KPDGYPWDVHACDM-UHFFFAOYSA-N 4-(5-methyl-2-propan-2-ylphenoxy)phenol Chemical compound CC(C)C1=CC=C(C)C=C1OC1=CC=C(O)C=C1 KPDGYPWDVHACDM-UHFFFAOYSA-N 0.000 description 1
AMGUOKBZLVNNLG-UHFFFAOYSA-N 4-[2-bromo-4-(trifluoromethyl)phenoxy]phenol Chemical compound C1=CC(O)=CC=C1OC1=CC=C(C(F)(F)F)C=C1Br AMGUOKBZLVNNLG-UHFFFAOYSA-N 0.000 description 1
XKBVEHVQDYRJCW-UHFFFAOYSA-N 4-[2-chloro-4-(trifluoromethyl)phenoxy]phenol Chemical compound C1=CC(O)=CC=C1OC1=CC=C(C(F)(F)F)C=C1Cl XKBVEHVQDYRJCW-UHFFFAOYSA-N 0.000 description 1
IWLRGEKAYJALDI-UHFFFAOYSA-N 4-[2-nitro-4-(trifluoromethyl)phenoxy]phenol Chemical compound C1=CC(O)=CC=C1OC1=CC=C(C(F)(F)F)C=C1[N+]([O-])=O IWLRGEKAYJALDI-UHFFFAOYSA-N 0.000 description 1
QBUZGHPDFUNKIZ-UHFFFAOYSA-N 4-[3-(trifluoromethyl)phenoxy]phenol Chemical compound C1=CC(O)=CC=C1OC1=CC=CC(C(F)(F)F)=C1 QBUZGHPDFUNKIZ-UHFFFAOYSA-N 0.000 description 1
WZJADCRYEHOFBZ-UHFFFAOYSA-N 5-bromohept-3-enoic acid Chemical compound CCC(Br)C=CCC(O)=O WZJADCRYEHOFBZ-UHFFFAOYSA-N 0.000 description 1
NGXYRRAUEFXABL-UHFFFAOYSA-N 5-bromoheptanoic acid Chemical compound CCC(Br)CCCC(O)=O NGXYRRAUEFXABL-UHFFFAOYSA-N 0.000 description 1
WHSKFQVUTWQVLC-UHFFFAOYSA-N 5-bromohex-3-enoic acid Chemical compound CC(Br)C=CCC(O)=O WHSKFQVUTWQVLC-UHFFFAOYSA-N 0.000 description 1
XCUYAMBYVMRCSR-UHFFFAOYSA-N 5-bromohexanoic acid Chemical compound CC(Br)CCCC(O)=O XCUYAMBYVMRCSR-UHFFFAOYSA-N 0.000 description 1
COGFIAQRXUMRLW-UHFFFAOYSA-N 5-bromooct-3-enoic acid Chemical compound BrC(C=CCC(=O)O)CCC COGFIAQRXUMRLW-UHFFFAOYSA-N 0.000 description 1
ZATRXUOATJAZHJ-UHFFFAOYSA-N 5-bromooctanoic acid Chemical compound CCCC(Br)CCCC(O)=O ZATRXUOATJAZHJ-UHFFFAOYSA-N 0.000 description 1
UCNTZGVLKRZSRF-UHFFFAOYSA-N 5-chloro-2-(4-hydroxyphenoxy)benzonitrile Chemical compound C1=CC(O)=CC=C1OC1=CC=C(Cl)C=C1C#N UCNTZGVLKRZSRF-UHFFFAOYSA-N 0.000 description 1
QAXDJKWZEQLOER-UHFFFAOYSA-N 5-chloroheptanoic acid Chemical compound CCC(Cl)CCCC(O)=O QAXDJKWZEQLOER-UHFFFAOYSA-N 0.000 description 1
XAAZJIWABWKJGO-UHFFFAOYSA-N 5-chlorohex-3-enoic acid Chemical compound CC(Cl)C=CCC(O)=O XAAZJIWABWKJGO-UHFFFAOYSA-N 0.000 description 1
BKYXJMPZIUFVJA-UHFFFAOYSA-N 5-chlorohexanoic acid Chemical compound CC(Cl)CCCC(O)=O BKYXJMPZIUFVJA-UHFFFAOYSA-N 0.000 description 1
TXXUCGCNYVUMFQ-UHFFFAOYSA-N 5-chlorooctanoic acid Chemical compound CCCC(Cl)CCCC(O)=O TXXUCGCNYVUMFQ-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
GWODJZDRIIYNRR-UHFFFAOYSA-N BrC(C(=O)OC)C.C1(=CC=CC=C1)O Chemical compound BrC(C(=O)OC)C.C1(=CC=CC=C1)O GWODJZDRIIYNRR-UHFFFAOYSA-N 0.000 description 1
SXMQDCRCUUKQRF-UHFFFAOYSA-N BrC(C(=O)OCC)CC.[N+](=O)([O-])C1=CC=C(OC2=CC=C(C=C2)O)C=C1 Chemical compound BrC(C(=O)OCC)CC.[N+](=O)([O-])C1=CC=C(OC2=CC=C(C=C2)O)C=C1 SXMQDCRCUUKQRF-UHFFFAOYSA-N 0.000 description 1
RZQAEEOVQOBIIN-UHFFFAOYSA-N BrCC(=O)OCC.ClC1=C(OC2=CC=C(C=C2)O)C=CC(=C1)[N+](=O)[O-] Chemical compound BrCC(=O)OCC.ClC1=C(OC2=CC=C(C=C2)O)C=CC(=C1)[N+](=O)[O-] RZQAEEOVQOBIIN-UHFFFAOYSA-N 0.000 description 1
SLIUXWIVTWHOHD-UHFFFAOYSA-N BrCC=CC(=O)OCC.[N+](=O)([O-])C1=C(OC2=CC=C(C=C2)O)C=CC(=C1)Cl Chemical compound BrCC=CC(=O)OCC.[N+](=O)([O-])C1=C(OC2=CC=C(C=C2)O)C=CC(=C1)Cl SLIUXWIVTWHOHD-UHFFFAOYSA-N 0.000 description 1
FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
RPAJLJXIFUJZIC-UHFFFAOYSA-N C1(=CC=CC=C1)O.C(C)OC(C(C)Br)=O Chemical compound C1(=CC=CC=C1)O.C(C)OC(C(C)Br)=O RPAJLJXIFUJZIC-UHFFFAOYSA-N 0.000 description 1
KXZJVNAQDGQDDA-UHFFFAOYSA-N C1(=CC=CC=C1)O.ClCC(=O)O Chemical compound C1(=CC=CC=C1)O.ClCC(=O)O KXZJVNAQDGQDDA-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
DZGDBGULTWRWOY-UHFFFAOYSA-N ClCC(=O)OC.C1(=CC=CC=C1)O Chemical compound ClCC(=O)OC.C1(=CC=CC=C1)O DZGDBGULTWRWOY-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-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
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
BKAOCUJXRWCECQ-UHFFFAOYSA-N [4-(trifluoromethyl)phenyl] 2-phenoxypent-2-eneperoxoate Chemical compound O(C1=CC=CC=C1)C(C(=O)OOC1=CC=C(C=C1)C(F)(F)F)=CCC BKAOCUJXRWCECQ-UHFFFAOYSA-N 0.000 description 1
CBIIVSNVIRRJAS-UHFFFAOYSA-N [C].CCC Chemical compound [C].CCC CBIIVSNVIRRJAS-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
FEZISPWUKYOUDC-UHFFFAOYSA-M azanium tetrabutylazanium dichloride Chemical compound [NH4+].[Cl-].[Cl-].CCCC[N+](CCCC)(CCCC)CCCC FEZISPWUKYOUDC-UHFFFAOYSA-M 0.000 description 1
VEFXTGTZJOWDOF-UHFFFAOYSA-N benzene;hydrate Chemical compound O.C1=CC=CC=C1 VEFXTGTZJOWDOF-UHFFFAOYSA-N 0.000 description 1
VJGNLOIQCWLBJR-UHFFFAOYSA-M benzyl(tributyl)azanium;chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CC1=CC=CC=C1 VJGNLOIQCWLBJR-UHFFFAOYSA-M 0.000 description 1
KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 1
MPCZUKWSZFWNBV-UHFFFAOYSA-M benzyl(tripentyl)azanium;chloride Chemical compound [Cl-].CCCCC[N+](CCCCC)(CCCCC)CC1=CC=CC=C1 MPCZUKWSZFWNBV-UHFFFAOYSA-M 0.000 description 1
USFRYJRPHFMVBZ-UHFFFAOYSA-M benzyl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)CC1=CC=CC=C1 USFRYJRPHFMVBZ-UHFFFAOYSA-M 0.000 description 1
KFXPEMZFTKVZQV-UHFFFAOYSA-N bromo pentanoate Chemical compound CCCCC(=O)OBr KFXPEMZFTKVZQV-UHFFFAOYSA-N 0.000 description 1
DKZLMRKANVHJGG-UHFFFAOYSA-N butyl 2-bromobutanoate Chemical compound CCCCOC(=O)C(Br)CC DKZLMRKANVHJGG-UHFFFAOYSA-N 0.000 description 1
IZXROSFURABXME-UHFFFAOYSA-N butyl 2-bromopentanoate Chemical compound CCCCOC(=O)C(Br)CCC IZXROSFURABXME-UHFFFAOYSA-N 0.000 description 1
INMAEXGIVZJYIJ-UHFFFAOYSA-N butyl 2-bromopropanoate Chemical compound CCCCOC(=O)C(C)Br INMAEXGIVZJYIJ-UHFFFAOYSA-N 0.000 description 1
NULLMNSLPQGSMJ-UHFFFAOYSA-N butyl 2-chlorobutanoate Chemical compound CCCCOC(=O)C(Cl)CC NULLMNSLPQGSMJ-UHFFFAOYSA-N 0.000 description 1
PMVCCUUEVYCMBN-UHFFFAOYSA-N butyl 2-chloropentanoate Chemical compound CCCCOC(=O)C(Cl)CCC PMVCCUUEVYCMBN-UHFFFAOYSA-N 0.000 description 1
KATNUXHENWPMQJ-UHFFFAOYSA-N butyl 2-chloropropanoate Chemical compound CCCCOC(=O)C(C)Cl KATNUXHENWPMQJ-UHFFFAOYSA-N 0.000 description 1
YEYPRQINUMURCL-UHFFFAOYSA-N butyl 4-bromohept-2-enoate Chemical compound CCCCOC(=O)C=CC(Br)CCC YEYPRQINUMURCL-UHFFFAOYSA-N 0.000 description 1
WVWJQEBDLMFLGW-UHFFFAOYSA-N butyl 4-bromoheptanoate Chemical compound CCCCOC(=O)CCC(Br)CCC WVWJQEBDLMFLGW-UHFFFAOYSA-N 0.000 description 1
CISSIIGHHXWPNB-UHFFFAOYSA-N butyl 4-bromohexanoate Chemical compound CCCCOC(=O)CCC(Br)CC CISSIIGHHXWPNB-UHFFFAOYSA-N 0.000 description 1
ASTFDVCLVALRAH-UHFFFAOYSA-N butyl 4-bromopent-2-enoate Chemical compound CCCCOC(=O)C=CC(C)Br ASTFDVCLVALRAH-UHFFFAOYSA-N 0.000 description 1
NDPVPNNUQXJJTF-UHFFFAOYSA-N butyl 4-bromopentanoate Chemical compound CCCCOC(=O)CCC(C)Br NDPVPNNUQXJJTF-UHFFFAOYSA-N 0.000 description 1
FUMMMMCAIINITK-UHFFFAOYSA-N butyl 4-chlorohept-2-enoate Chemical compound CCCCOC(=O)C=CC(Cl)CCC FUMMMMCAIINITK-UHFFFAOYSA-N 0.000 description 1
RMPSYSRXPLQXEI-UHFFFAOYSA-N butyl 4-chloroheptanoate Chemical compound CCCCOC(=O)CCC(Cl)CCC RMPSYSRXPLQXEI-UHFFFAOYSA-N 0.000 description 1
YJADGCAMTGKMAK-UHFFFAOYSA-N butyl 4-chlorohexanoate Chemical compound CCCCOC(=O)CCC(Cl)CC YJADGCAMTGKMAK-UHFFFAOYSA-N 0.000 description 1
UJNOAAMUQUJECO-UHFFFAOYSA-N butyl 4-chloropent-2-enoate Chemical compound CCCCOC(=O)C=CC(C)Cl UJNOAAMUQUJECO-UHFFFAOYSA-N 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
IKWKJIWDLVYZIY-UHFFFAOYSA-M butyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCC)C1=CC=CC=C1 IKWKJIWDLVYZIY-UHFFFAOYSA-M 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
239000000920 calcium hydroxide Substances 0.000 description 1
229910001861 calcium hydroxide Inorganic materials 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
MVPPADPHJFYWMZ-IDEBNGHGSA-N chlorobenzene Chemical group Cl[13C]1=[13CH][13CH]=[13CH][13CH]=[13CH]1 MVPPADPHJFYWMZ-IDEBNGHGSA-N 0.000 description 1
229940117389 dichlorobenzene Drugs 0.000 description 1
XIMFCGSNSKXPBO-UHFFFAOYSA-N ethyl 2-bromobutanoate Chemical compound CCOC(=O)C(Br)CC XIMFCGSNSKXPBO-UHFFFAOYSA-N 0.000 description 1
QTEITWPJVHAOTN-UHFFFAOYSA-N ethyl 2-chlorobutanoate Chemical compound CCOC(=O)C(Cl)CC QTEITWPJVHAOTN-UHFFFAOYSA-N 0.000 description 1
ZAOIIUSDMKVQJW-UHFFFAOYSA-N ethyl 2-chloropentanoate Chemical compound CCCC(Cl)C(=O)OCC ZAOIIUSDMKVQJW-UHFFFAOYSA-N 0.000 description 1
JEAVBVKAYUCPAQ-UHFFFAOYSA-N ethyl 2-chloropropanoate Chemical compound CCOC(=O)C(C)Cl JEAVBVKAYUCPAQ-UHFFFAOYSA-N 0.000 description 1
NEHGWVYDSJWTJK-UHFFFAOYSA-N ethyl 4-[4-[4-(trifluoromethyl)phenoxy]phenoxy]pent-2-enoate Chemical compound C1=CC(OC(C)C=CC(=O)OCC)=CC=C1OC1=CC=C(C(F)(F)F)C=C1 NEHGWVYDSJWTJK-UHFFFAOYSA-N 0.000 description 1
IKIHKQGHJBVQDE-UHFFFAOYSA-N ethyl 4-bromohept-2-enoate Chemical compound CCCC(Br)C=CC(=O)OCC IKIHKQGHJBVQDE-UHFFFAOYSA-N 0.000 description 1
XJZJWVDNNVYAGZ-UHFFFAOYSA-N ethyl 4-bromoheptanoate Chemical compound CCCC(Br)CCC(=O)OCC XJZJWVDNNVYAGZ-UHFFFAOYSA-N 0.000 description 1
ZJZQUQNWVJGJGO-UHFFFAOYSA-N ethyl 4-bromohex-2-enoate Chemical compound CCOC(=O)C=CC(Br)CC ZJZQUQNWVJGJGO-UHFFFAOYSA-N 0.000 description 1
IOGMSMCKZKGXMW-UHFFFAOYSA-N ethyl 4-bromohexanoate Chemical compound CCOC(=O)CCC(Br)CC IOGMSMCKZKGXMW-UHFFFAOYSA-N 0.000 description 1
CTVCPHLFHPQRNF-UHFFFAOYSA-N ethyl 4-bromopentanoate Chemical compound CCOC(=O)CCC(C)Br CTVCPHLFHPQRNF-UHFFFAOYSA-N 0.000 description 1
GTWSSFMEZVKCDW-UHFFFAOYSA-N ethyl 4-chlorohept-2-enoate Chemical compound CCCC(Cl)C=CC(=O)OCC GTWSSFMEZVKCDW-UHFFFAOYSA-N 0.000 description 1
IIHJTISRWPLKMO-UHFFFAOYSA-N ethyl 4-chlorohex-2-enoate Chemical compound CCOC(=O)C=CC(Cl)CC IIHJTISRWPLKMO-UHFFFAOYSA-N 0.000 description 1
WFDPRNSJUFGSSQ-UHFFFAOYSA-N ethyl 4-chlorohexanoate Chemical compound CCOC(=O)CCC(Cl)CC WFDPRNSJUFGSSQ-UHFFFAOYSA-N 0.000 description 1
OJAYUEGXOWQYTB-UHFFFAOYSA-N ethyl 4-chloropentanoate Chemical compound CCOC(=O)CCC(C)Cl OJAYUEGXOWQYTB-UHFFFAOYSA-N 0.000 description 1
238000000605 extraction Methods 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000012433 hydrogen halide Substances 0.000 description 1
229910000039 hydrogen halide Inorganic materials 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
150000002681 magnesium compounds Chemical class 0.000 description 1
239000000395 magnesium oxide Substances 0.000 description 1
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
MCVVUJPXSBQTRZ-ONEGZZNKSA-N methyl (e)-but-2-enoate Chemical compound COC(=O)\C=C\C MCVVUJPXSBQTRZ-ONEGZZNKSA-N 0.000 description 1
UFQQDNMQADCHGH-UHFFFAOYSA-N methyl 2-bromobutanoate Chemical compound CCC(Br)C(=O)OC UFQQDNMQADCHGH-UHFFFAOYSA-N 0.000 description 1
MGMWQSVSOGNGPL-UHFFFAOYSA-N methyl 2-bromopentanoate Chemical compound CCCC(Br)C(=O)OC MGMWQSVSOGNGPL-UHFFFAOYSA-N 0.000 description 1
ACEONLNNWKIPTM-UHFFFAOYSA-N methyl 2-bromopropanoate Chemical compound COC(=O)C(C)Br ACEONLNNWKIPTM-UHFFFAOYSA-N 0.000 description 1
BHQQXAOBIZQEGI-UHFFFAOYSA-N methyl 2-chlorobutanoate Chemical compound CCC(Cl)C(=O)OC BHQQXAOBIZQEGI-UHFFFAOYSA-N 0.000 description 1
DFJFGBSFTBCENV-UHFFFAOYSA-N methyl 2-chloropentanoate Chemical compound CCCC(Cl)C(=O)OC DFJFGBSFTBCENV-UHFFFAOYSA-N 0.000 description 1
MNSSCJPWMNHFCX-UHFFFAOYSA-N methyl 4-bromoheptanoate Chemical compound CCCC(Br)CCC(=O)OC MNSSCJPWMNHFCX-UHFFFAOYSA-N 0.000 description 1
ITUFMJJVKOEQSC-UHFFFAOYSA-N methyl 4-bromohex-2-enoate Chemical compound CCC(Br)C=CC(=O)OC ITUFMJJVKOEQSC-UHFFFAOYSA-N 0.000 description 1
YUQJMLVATSOGQG-UHFFFAOYSA-N methyl 4-bromohexanoate Chemical compound CCC(Br)CCC(=O)OC YUQJMLVATSOGQG-UHFFFAOYSA-N 0.000 description 1
NSJYALNSMYWWIY-UHFFFAOYSA-N methyl 4-bromopent-2-enoate Chemical compound COC(=O)C=CC(C)Br NSJYALNSMYWWIY-UHFFFAOYSA-N 0.000 description 1
PUULUFJRBAIMQE-UHFFFAOYSA-N methyl 4-bromopentanoate Chemical compound COC(=O)CCC(C)Br PUULUFJRBAIMQE-UHFFFAOYSA-N 0.000 description 1
FNSGNNZYMUIWAD-UHFFFAOYSA-N methyl 4-chloro-3-methylbut-2-enoate Chemical compound COC(=O)C=C(C)CCl FNSGNNZYMUIWAD-UHFFFAOYSA-N 0.000 description 1
FSDAIIRCQHQFAJ-UHFFFAOYSA-N methyl 4-chlorohept-2-enoate Chemical compound CCCC(Cl)C=CC(=O)OC FSDAIIRCQHQFAJ-UHFFFAOYSA-N 0.000 description 1
CFWLQQGNSUHNAP-UHFFFAOYSA-N methyl 4-chlorohex-2-enoate Chemical compound CCC(Cl)C=CC(=O)OC CFWLQQGNSUHNAP-UHFFFAOYSA-N 0.000 description 1
DHKHERPAWHFRPE-UHFFFAOYSA-N methyl 4-chlorohexanoate Chemical compound CCC(Cl)CCC(=O)OC DHKHERPAWHFRPE-UHFFFAOYSA-N 0.000 description 1
BWKWOSMMSXXDGL-UHFFFAOYSA-N methyl 4-chloropent-2-enoate Chemical compound COC(=O)C=CC(C)Cl BWKWOSMMSXXDGL-UHFFFAOYSA-N 0.000 description 1
UHNCLQCIKXIBSA-UHFFFAOYSA-N methyl 4-chloropentanoate Chemical compound COC(=O)CCC(C)Cl UHNCLQCIKXIBSA-UHFFFAOYSA-N 0.000 description 1
LSEFCHWGJNHZNT-UHFFFAOYSA-M methyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 LSEFCHWGJNHZNT-UHFFFAOYSA-M 0.000 description 1
XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 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
239000012044 organic layer Substances 0.000 description 1
YIYBQIKDCADOSF-UHFFFAOYSA-N pent-2-enoic acid Chemical compound CCC=CC(O)=O YIYBQIKDCADOSF-UHFFFAOYSA-N 0.000 description 1
239000012071 phase Substances 0.000 description 1
238000005191 phase separation Methods 0.000 description 1
LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 1
XFUVLNBRVDDVPI-UHFFFAOYSA-N phenyl pentaneperoxoate Chemical compound O(C1=CC=CC=C1)OC(CCCC)=O XFUVLNBRVDDVPI-UHFFFAOYSA-N 0.000 description 1
150000003112 potassium compounds Chemical class 0.000 description 1
BJPYPGKBFMZGDQ-UHFFFAOYSA-N propyl 2-bromobutanoate Chemical compound CCCOC(=O)C(Br)CC BJPYPGKBFMZGDQ-UHFFFAOYSA-N 0.000 description 1
KOAGPWABJORAAF-UHFFFAOYSA-N propyl 2-bromopentanoate Chemical compound CCCOC(=O)C(Br)CCC KOAGPWABJORAAF-UHFFFAOYSA-N 0.000 description 1
GDPGCHFFZZXKTQ-UHFFFAOYSA-N propyl 2-bromopropanoate Chemical compound CCCOC(=O)C(C)Br GDPGCHFFZZXKTQ-UHFFFAOYSA-N 0.000 description 1
NZHZYDSYLLWKOK-UHFFFAOYSA-N propyl 2-chlorobutanoate Chemical compound CCCOC(=O)C(Cl)CC NZHZYDSYLLWKOK-UHFFFAOYSA-N 0.000 description 1
HUBXULUFSOZRDU-UHFFFAOYSA-N propyl 2-chloropentanoate Chemical compound CCCOC(=O)C(Cl)CCC HUBXULUFSOZRDU-UHFFFAOYSA-N 0.000 description 1
HSPJTAFAQSJQQY-UHFFFAOYSA-N propyl 4-bromo-3-methylbut-2-enoate Chemical compound CCCOC(=O)C=C(C)CBr HSPJTAFAQSJQQY-UHFFFAOYSA-N 0.000 description 1
BNKUJZUTOFDAGR-UHFFFAOYSA-N propyl 4-bromohept-2-enoate Chemical compound CCCOC(=O)C=CC(Br)CCC BNKUJZUTOFDAGR-UHFFFAOYSA-N 0.000 description 1
XBKKECHBDIBDQY-UHFFFAOYSA-N propyl 4-bromohex-2-enoate Chemical compound CCCOC(=O)C=CC(Br)CC XBKKECHBDIBDQY-UHFFFAOYSA-N 0.000 description 1
HCFXXMIMLNQLOC-UHFFFAOYSA-N propyl 4-bromohexanoate Chemical compound CCCOC(=O)CCC(Br)CC HCFXXMIMLNQLOC-UHFFFAOYSA-N 0.000 description 1
QJHJTJMEFXFALN-UHFFFAOYSA-N propyl 4-bromopent-2-enoate Chemical compound CCCOC(=O)C=CC(C)Br QJHJTJMEFXFALN-UHFFFAOYSA-N 0.000 description 1
DTAKVNYIQXYOOI-UHFFFAOYSA-N propyl 4-bromopentanoate Chemical compound CCCOC(=O)CCC(C)Br DTAKVNYIQXYOOI-UHFFFAOYSA-N 0.000 description 1
YVUAQWHDFOBODJ-UHFFFAOYSA-N propyl 4-chlorohept-2-enoate Chemical compound CCCOC(=O)C=CC(Cl)CCC YVUAQWHDFOBODJ-UHFFFAOYSA-N 0.000 description 1
DWMKIWSTFZZSNS-UHFFFAOYSA-N propyl 4-chloroheptanoate Chemical compound CCCOC(=O)CCC(Cl)CCC DWMKIWSTFZZSNS-UHFFFAOYSA-N 0.000 description 1
DXWBFPGGUHMOEC-UHFFFAOYSA-N propyl 4-chlorohex-2-enoate Chemical compound CCCOC(=O)C=CC(Cl)CC DXWBFPGGUHMOEC-UHFFFAOYSA-N 0.000 description 1
PYZRTOPJCSHVPP-UHFFFAOYSA-N propyl 4-chlorohexanoate Chemical compound CCCOC(=O)CCC(Cl)CC PYZRTOPJCSHVPP-UHFFFAOYSA-N 0.000 description 1
VJIJGMXEJLSHIS-UHFFFAOYSA-N propyl 4-chloropent-2-enoate Chemical compound CCCOC(=O)C=CC(C)Cl VJIJGMXEJLSHIS-UHFFFAOYSA-N 0.000 description 1
GMMJOPYCLIFFIO-UHFFFAOYSA-N propyl 4-chloropentanoate Chemical compound CCCOC(=O)CCC(C)Cl GMMJOPYCLIFFIO-UHFFFAOYSA-N 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
POECFFCNUXZPJT-UHFFFAOYSA-M sodium;carbonic acid;hydrogen carbonate Chemical compound [Na+].OC(O)=O.OC([O-])=O POECFFCNUXZPJT-UHFFFAOYSA-M 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
RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 0.000 description 1
IBWGNZVCJVLSHB-UHFFFAOYSA-M tetrabutylphosphanium;chloride Chemical compound [Cl-].CCCC[P+](CCCC)(CCCC)CCCC IBWGNZVCJVLSHB-UHFFFAOYSA-M 0.000 description 1
CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
SYZCZDCAEVUSPM-UHFFFAOYSA-M tetrahexylazanium;bromide Chemical compound [Br-].CCCCCC[N+](CCCCCC)(CCCCCC)CCCCCC SYZCZDCAEVUSPM-UHFFFAOYSA-M 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
SPALIFXDWQTXKS-UHFFFAOYSA-M tetrapentylazanium;bromide Chemical compound [Br-].CCCCC[N+](CCCCC)(CCCCC)CCCCC SPALIFXDWQTXKS-UHFFFAOYSA-M 0.000 description 1
SXAWRMKQZKPHNJ-UHFFFAOYSA-M tetrapentylazanium;chloride Chemical compound [Cl-].CCCCC[N+](CCCCC)(CCCCC)CCCCC SXAWRMKQZKPHNJ-UHFFFAOYSA-M 0.000 description 1
BGQMOFGZRJUORO-UHFFFAOYSA-M tetrapropylammonium bromide Chemical compound [Br-].CCC[N+](CCC)(CCC)CCC BGQMOFGZRJUORO-UHFFFAOYSA-M 0.000 description 1
RYVBINGWVJJDPU-UHFFFAOYSA-M tributyl(hexadecyl)phosphanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[P+](CCCC)(CCCC)CCCC RYVBINGWVJJDPU-UHFFFAOYSA-M 0.000 description 1
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
Oil, Petroleum & Natural Gas (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

NL7907749A 1978-11-01 1979-10-22 Werkwijze voor het bereiden van een fenoxycarbonzuurderivaat. NL7907749A (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP13506078A JPS5562043A (en)	1978-11-01	1978-11-01	Preparation of phenoxycarboxylic acid derivative
JP13506078		1978-11-01

Publications (1)

Publication Number	Publication Date
NL7907749A true NL7907749A (nl)	1980-05-06

Family

ID=15142947

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL7907749A NL7907749A (nl)	1978-11-01	1979-10-22	Werkwijze voor het bereiden van een fenoxycarbonzuurderivaat.

Country Status (15)

Country	Link
US (1)	US4254262A (fr)
JP (1)	JPS5562043A (fr)
AU (1)	AU531187B2 (fr)
BR (1)	BR7907070A (fr)
DE (1)	DE2942989A1 (fr)
ES (1)	ES485593A1 (fr)
FR (1)	FR2440352A1 (fr)
GB (1)	GB2035317B (fr)
HU (1)	HU182584B (fr)
IL (1)	IL58492A0 (fr)
IN (1)	IN151554B (fr)
IT (1)	IT1124869B (fr)
NL (1)	NL7907749A (fr)
OA (1)	OA06369A (fr)
SU (1)	SU1068032A3 (fr)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0058173B1 (fr) *	1980-08-26	1984-12-05	Ici Australia Limited	Procede de synthese de derives aryloxy
JPS5931749A (ja) *	1982-08-17	1984-02-20	Kanesho Kk	シアノフエノキシフエノキシペンテン酸誘導体、その製造法及び該化合物を含有する除草剤
DE3236730A1 (de) *	1982-10-04	1984-04-05	Hoechst Ag, 6230 Frankfurt	Verfahren zur herstellung von benzoxazolyl- und benzthiazolyloxyphenoxypropionsaeurederivaten
US4608081A (en) *	1984-06-22	1986-08-26	Kanesho Company Limited	Herbicidal 2-[4-(4-cyanophenoxy)-phenoxy]-alkanoic acid amides
US4661617A (en) *	1985-04-19	1987-04-28	Sandoz Ltd.	Novel compositions
EP0391451A1 (fr) *	1986-04-17	1990-10-10	Imperial Chemical Industries Plc	Fongicides
US4701531A (en) *	1986-12-01	1987-10-20	The Dow Chemical Company	Catalyzed alkylation of halopyridinates in the absence of added organic solvents
DE3880544D1 (de) *	1987-04-21	1993-06-03	Basf Ag	P-phenoxy-phenoxymethyl-fuenfring-heteroaromaten.
JPH0791217B2 (ja) *	1988-11-21	1995-10-04	宇部興産株式会社	光学活性な２−フェノキシブタン酸の製造法
IT1265087B1 (it) *	1993-05-20	1996-10-30	Recordati Chem Pharm	Processo per la preparazione di gemfibrozil

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3972887A (en) *	1972-12-11	1976-08-03	The Dow Chemical Company	Process for preparing phosphorothioates and phenylphosponothioates
DE2342118C2 (de) *	1973-08-21	1982-09-23	Merck Patent Gmbh, 6100 Darmstadt	Phenoxypropionsäurederivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende pharmazeutische Zubereitungen
JPS52131540A (en) *	1976-04-14	1977-11-04	Ishihara Sangyo Kaisha Ltd	Phenoxyvaleric acid derivatives and herbicides therefrom
JPS52131542A (en) *	1976-04-28	1977-11-04	Ishihara Sangyo Kaisha Ltd	Phenoxypropionic acid derivatives and herbicides containing them

1978
- 1978-11-01 JP JP13506078A patent/JPS5562043A/ja active Pending
1979
- 1979-10-11 AU AU51629/79A patent/AU531187B2/en not_active Ceased
- 1979-10-12 US US06/084,164 patent/US4254262A/en not_active Expired - Lifetime
- 1979-10-18 IL IL58492A patent/IL58492A0/xx unknown
- 1979-10-22 NL NL7907749A patent/NL7907749A/nl not_active Application Discontinuation
- 1979-10-23 FR FR7926238A patent/FR2440352A1/fr active Granted
- 1979-10-24 DE DE19792942989 patent/DE2942989A1/de not_active Withdrawn
- 1979-10-26 HU HU79IA860A patent/HU182584B/hu unknown
- 1979-10-30 IN IN1128/CAL/79A patent/IN151554B/en unknown
- 1979-10-31 ES ES485593A patent/ES485593A1/es not_active Expired
- 1979-10-31 IT IT26964/79A patent/IT1124869B/it active
- 1979-10-31 SU SU792836785A patent/SU1068032A3/ru active
- 1979-10-31 BR BR7907070A patent/BR7907070A/pt not_active IP Right Cessation
- 1979-11-01 GB GB7937945A patent/GB2035317B/en not_active Expired
- 1979-11-01 OA OA56929A patent/OA06369A/fr unknown

Also Published As

Publication number	Publication date
HU182584B (en)	1984-02-28
IL58492A0 (en)	1980-01-31
ES485593A1 (es)	1980-07-01
SU1068032A3 (ru)	1984-01-15
JPS5562043A (en)	1980-05-10
DE2942989A1 (de)	1980-05-14
IT1124869B (it)	1986-05-14
BR7907070A (pt)	1980-07-15
FR2440352B1 (fr)	1984-08-10
FR2440352A1 (fr)	1980-05-30
AU531187B2 (en)	1983-08-11
IT7926964A0 (it)	1979-10-31
AU5162979A (en)	1980-05-08
GB2035317B (en)	1983-01-12
OA06369A (fr)	1981-08-31
IN151554B (fr)	1983-05-21
US4254262A (en)	1981-03-03
GB2035317A (en)	1980-06-18

Legal Events

Date	Code	Title	Description
1985-01-01	A85	Still pending on 85-01-01
1985-06-03	BV	The patent application has lapsed

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