CA1224796A - Synthese des derives de phenoxyalkane - Google Patents

Synthese des derives de phenoxyalkane

Info

Publication number: CA1224796A
Authority: CA; Canada
Prior art keywords: group; chosen; formula; alkyl; compound
Prior art date: 1981-09-04
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA000385290A

Other languages

English (en)

Inventor

Keith G. Watson

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Orica Ltd

Original Assignee

ICI Australia Ltd

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.)

1981-09-04

Filing date

1981-09-04

Publication date

1987-07-28

1981-09-04 Application filed by ICI Australia Ltd filed Critical ICI Australia Ltd

1981-09-04 Priority to CA000385290A priority Critical patent/CA1224796A/fr

1987-07-28 Application granted granted Critical

1987-07-28 Publication of CA1224796A publication Critical patent/CA1224796A/fr

Status Expired legal-status Critical Current

Links

230000015572 biosynthetic process Effects 0.000 title claims abstract description 11
238000003786 synthesis reaction Methods 0.000 title claims abstract description 10
-1 sulfate ester Chemical class 0.000 claims abstract description 74
238000000034 method Methods 0.000 claims abstract description 51
230000008569 process Effects 0.000 claims abstract description 50
150000001875 compounds Chemical class 0.000 claims abstract description 41
125000003545 alkoxy group Chemical group 0.000 claims abstract description 28
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 24
239000001257 hydrogen Substances 0.000 claims abstract description 24
150000002431 hydrogen Chemical class 0.000 claims abstract description 16
238000007254 oxidation reaction Methods 0.000 claims abstract description 13
229910052736 halogen Inorganic materials 0.000 claims abstract description 11
150000002367 halogens Chemical class 0.000 claims abstract description 11
230000003647 oxidation Effects 0.000 claims abstract description 11
125000001424 substituent group Chemical group 0.000 claims abstract description 11
125000000217 alkyl group Chemical group 0.000 claims abstract description 9
150000001768 cations Chemical group 0.000 claims abstract description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
230000003301 hydrolyzing effect Effects 0.000 claims abstract description 6
239000000460 chlorine Substances 0.000 claims description 62
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 36
239000002253 acid Substances 0.000 claims description 21
125000001188 haloalkyl group Chemical group 0.000 claims description 16
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
239000002904 solvent Substances 0.000 claims description 15
150000003839 salts Chemical class 0.000 claims description 13
125000004093 cyano group Chemical group *C#N 0.000 claims description 9
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
150000001340 alkali metals Chemical class 0.000 claims description 8
125000004414 alkyl thio group Chemical group 0.000 claims description 8
AQIHDXGKQHFBNW-UHFFFAOYSA-N 2-(4-hydroxyphenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(O)C=C1 AQIHDXGKQHFBNW-UHFFFAOYSA-N 0.000 claims description 7
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 6
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
125000004438 haloalkoxy group Chemical group 0.000 claims description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
229910052500 inorganic mineral Inorganic materials 0.000 claims description 6
239000000463 material Substances 0.000 claims description 6
239000011707 mineral Substances 0.000 claims description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
150000007524 organic acids Chemical class 0.000 claims description 6
239000003960 organic solvent Substances 0.000 claims description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 5
229910001413 alkali metal ion Inorganic materials 0.000 claims description 5
125000003302 alkenyloxy group Chemical group 0.000 claims description 5
125000005133 alkynyloxy group Chemical group 0.000 claims description 5
229910052801 chlorine Inorganic materials 0.000 claims description 5
125000000623 heterocyclic group Chemical group 0.000 claims description 5
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 5
150000004968 peroxymonosulfuric acids Chemical class 0.000 claims description 5
229910052700 potassium Inorganic materials 0.000 claims description 5
239000011591 potassium Substances 0.000 claims description 5
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims description 4
229910001420 alkaline earth metal ion Inorganic materials 0.000 claims description 4
239000012670 alkaline solution Substances 0.000 claims description 4
125000005108 alkenylthio group Chemical group 0.000 claims description 4
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
125000005109 alkynylthio group Chemical group 0.000 claims description 4
150000004649 carbonic acid derivatives Chemical class 0.000 claims description 4
150000007529 inorganic bases Chemical class 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
150000007530 organic bases Chemical class 0.000 claims description 4
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
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 claims description 3
239000003513 alkali Substances 0.000 claims description 3
229910052783 alkali metal Inorganic materials 0.000 claims description 3
229910000272 alkali metal oxide Inorganic materials 0.000 claims description 3
125000001118 alkylidene group Chemical group 0.000 claims description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
229910052794 bromium Inorganic materials 0.000 claims description 3
125000000000 cycloalkoxy group Chemical group 0.000 claims description 3
230000001590 oxidative effect Effects 0.000 claims description 3
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
229910052708 sodium Inorganic materials 0.000 claims description 3
239000011734 sodium Substances 0.000 claims description 3
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
125000000656 azaniumyl group Chemical group [H][N+]([H])([H])[*] 0.000 claims description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
125000000262 haloalkenyl group Chemical group 0.000 claims description 2
125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 claims description 2
239000007800 oxidant agent Substances 0.000 claims description 2
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 2
125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 2
229910052784 alkaline earth metal Inorganic materials 0.000 claims 2
239000011630 iodine Substances 0.000 claims 2
229910052740 iodine Inorganic materials 0.000 claims 2
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
SYKNUAWMBRIEKB-UHFFFAOYSA-N [Cl].[Br] Chemical compound [Cl].[Br] SYKNUAWMBRIEKB-UHFFFAOYSA-N 0.000 claims 1
150000001342 alkaline earth metals Chemical class 0.000 claims 1
125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract description 9
JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 abstract description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 abstract description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 29
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
238000004821 distillation Methods 0.000 description 17
239000000203 mixture Substances 0.000 description 17
239000011541 reaction mixture Substances 0.000 description 17
150000001335 aliphatic alkanes Chemical class 0.000 description 15
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
239000000243 solution Substances 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 10
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 9
239000000047 product Substances 0.000 description 8
239000007787 solid Substances 0.000 description 8
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 7
ILYSHPJWNMPBPE-UHFFFAOYSA-N ethyl 2-(4-hydroxyphenoxy)propanoate Chemical compound CCOC(=O)C(C)OC1=CC=C(O)C=C1 ILYSHPJWNMPBPE-UHFFFAOYSA-N 0.000 description 7
238000010992 reflux Methods 0.000 description 7
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
150000002148 esters Chemical class 0.000 description 6
229960000443 hydrochloric acid Drugs 0.000 description 6
235000011167 hydrochloric acid Nutrition 0.000 description 6
235000011181 potassium carbonates Nutrition 0.000 description 5
238000002360 preparation method Methods 0.000 description 5
XLHUBROMZOAQMV-UHFFFAOYSA-N 1,4-benzosemiquinone Chemical group [O]C1=CC=C(O)C=C1 XLHUBROMZOAQMV-UHFFFAOYSA-N 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
230000007062 hydrolysis Effects 0.000 description 4
238000006460 hydrolysis reaction Methods 0.000 description 4
229910000027 potassium carbonate Inorganic materials 0.000 description 4
238000001228 spectrum Methods 0.000 description 4
HFHFGHLXUCOHLN-UHFFFAOYSA-N 2-fluorophenol Chemical compound OC1=CC=CC=C1F HFHFGHLXUCOHLN-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
239000001569 carbon dioxide Substances 0.000 description 3
229910002092 carbon dioxide Inorganic materials 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
230000002363 herbicidal effect Effects 0.000 description 3
238000002955 isolation Methods 0.000 description 3
USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 3
KYQHUXZXYUBUPX-UHFFFAOYSA-M potassium;(4-hydroxyphenyl) sulfate Chemical compound [K+].OC1=CC=C(OS([O-])(=O)=O)C=C1 KYQHUXZXYUBUPX-UHFFFAOYSA-M 0.000 description 3
239000000843 powder Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 2
101150041968 CDC13 gene Proteins 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
150000001450 anions Chemical class 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
239000002585 base Substances 0.000 description 2
239000012043 crude product Substances 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000010828 elution Methods 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
235000010755 mineral Nutrition 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 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
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
241001072332 Monia Species 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
239000004159 Potassium persulphate Substances 0.000 description 1
241000212342 Sium Species 0.000 description 1
238000007171 acid catalysis Methods 0.000 description 1
238000005903 acid hydrolysis reaction Methods 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
125000005140 aralkylsulfonyl group Chemical group 0.000 description 1
125000004391 aryl sulfonyl group Chemical group 0.000 description 1
125000005279 aryl sulfonyloxy group Chemical group 0.000 description 1
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
UCKZQZDVQVFOHP-UHFFFAOYSA-N bromo propanoate Chemical compound CCC(=O)OBr UCKZQZDVQVFOHP-UHFFFAOYSA-N 0.000 description 1
MPNXVFDGEQKYAY-UHFFFAOYSA-N butyl 2-(4-hydroxyphenoxy)propanoate Chemical compound CCCCOC(=O)C(C)OC1=CC=C(O)C=C1 MPNXVFDGEQKYAY-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
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000002026 chloroform extract Substances 0.000 description 1
IQFVPQOLBLOTPF-HKXUKFGYSA-L congo red Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(/N=N/C3=CC=C(C=C3)C3=CC=C(C=C3)/N=N/C3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)N)=CC(S([O-])(=O)=O)=C21 IQFVPQOLBLOTPF-HKXUKFGYSA-L 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000003480 eluent Substances 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
239000000469 ethanolic extract Substances 0.000 description 1
RIPCNQLGJZLGFA-UHFFFAOYSA-N ethyl 2-(2-fluoro-4-hydroxyphenoxy)propanoate Chemical compound CCOC(=O)C(C)OC1=CC=C(O)C=C1F RIPCNQLGJZLGFA-UHFFFAOYSA-N 0.000 description 1
239000002024 ethyl acetate extract Substances 0.000 description 1
239000000284 extract Substances 0.000 description 1
238000000605 extraction Methods 0.000 description 1
UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical compound OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 description 1
238000004108 freeze drying Methods 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
125000004441 haloalkylsulfonyl group Chemical group 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
DUJSHDRWEILTHX-UHFFFAOYSA-N hydroxy phenyl sulfate Chemical class OOS(=O)(=O)OC1=CC=CC=C1 DUJSHDRWEILTHX-UHFFFAOYSA-N 0.000 description 1
125000002632 imidazolidinyl group Chemical group 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
229960004592 isopropanol Drugs 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
229910000000 metal hydroxide Inorganic materials 0.000 description 1
229910021645 metal ion Inorganic materials 0.000 description 1
229910044991 metal oxide Inorganic materials 0.000 description 1
150000004706 metal oxides Chemical class 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000003495 polar organic solvent Substances 0.000 description 1
235000019394 potassium persulphate Nutrition 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
150000005599 propionic acid derivatives Chemical class 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
FPXPQMOQWJZYBL-UHFFFAOYSA-M quinol sulfate(1-) Chemical compound OC1=CC=C(OS([O-])(=O)=O)C=C1 FPXPQMOQWJZYBL-UHFFFAOYSA-M 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000011084 recovery Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
PNGLEYLFMHGIQO-UHFFFAOYSA-M sodium;3-(n-ethyl-3-methoxyanilino)-2-hydroxypropane-1-sulfonate;dihydrate Chemical compound O.O.[Na+].[O-]S(=O)(=O)CC(O)CN(CC)C1=CC=CC(OC)=C1 PNGLEYLFMHGIQO-UHFFFAOYSA-M 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
125000003396 thiol group Chemical class [H]S* 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA000385290A 1981-09-04 1981-09-04 Synthese des derives de phenoxyalkane Expired CA1224796A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000385290A CA1224796A (fr)	1981-09-04	1981-09-04	Synthese des derives de phenoxyalkane

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000385290A CA1224796A (fr)	1981-09-04	1981-09-04	Synthese des derives de phenoxyalkane

Publications (1)

Publication Number	Publication Date
CA1224796A true CA1224796A (fr)	1987-07-28

Family

ID=4120883

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000385290A Expired CA1224796A (fr)	1981-09-04	1981-09-04	Synthese des derives de phenoxyalkane

Country Status (1)

Country	Link
CA (1)	CA1224796A (fr)

1981
- 1981-09-04 CA CA000385290A patent/CA1224796A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2004-07-28	MKEX	Expiry

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