SU623515A3 - Способ получени полиеновых соединений или их солей - Google Patents
Способ получени полиеновых соединений или их солейInfo
- Publication number
- SU623515A3 SU623515A3 SU752178997A SU2178997A SU623515A3 SU 623515 A3 SU623515 A3 SU 623515A3 SU 752178997 A SU752178997 A SU 752178997A SU 2178997 A SU2178997 A SU 2178997A SU 623515 A3 SU623515 A3 SU 623515A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- chloro
- chloride
- methoxy
- acid
- dimethyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 11
- 150000003839 salts Chemical class 0.000 title claims 7
- 150000004291 polyenes Chemical class 0.000 title 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 33
- 239000002253 acid Substances 0.000 claims 31
- -1 polyene compounds Chemical class 0.000 claims 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 22
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 18
- 125000004494 ethyl ester group Chemical group 0.000 claims 17
- 239000000243 solution Substances 0.000 claims 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 14
- 150000001875 compounds Chemical class 0.000 claims 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 12
- 239000000203 mixture Substances 0.000 claims 12
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims 11
- 239000011541 reaction mixture Substances 0.000 claims 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 10
- 229910052938 sodium sulfate Inorganic materials 0.000 claims 10
- 235000011152 sodium sulphate Nutrition 0.000 claims 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 9
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 9
- 238000009835 boiling Methods 0.000 claims 9
- 238000006243 chemical reaction Methods 0.000 claims 9
- 239000000284 extract Substances 0.000 claims 8
- 238000003756 stirring Methods 0.000 claims 8
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 7
- 230000003993 interaction Effects 0.000 claims 7
- 239000000155 melt Substances 0.000 claims 7
- 238000001953 recrystallisation Methods 0.000 claims 7
- 239000007858 starting material Substances 0.000 claims 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 6
- 239000000706 filtrate Substances 0.000 claims 6
- 239000000741 silica gel Substances 0.000 claims 6
- 229910002027 silica gel Inorganic materials 0.000 claims 6
- 238000001179 sorption measurement Methods 0.000 claims 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 5
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 239000003480 eluent Substances 0.000 claims 5
- 239000003960 organic solvent Substances 0.000 claims 5
- 239000000047 product Substances 0.000 claims 5
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 4
- 239000007864 aqueous solution Substances 0.000 claims 4
- 238000001816 cooling Methods 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 claims 4
- 239000002904 solvent Substances 0.000 claims 4
- LBRDQQPGFNRZGV-UHFFFAOYSA-N 1,1-dimethoxy-2-methylbut-3-en-2-ol Chemical compound COC(OC)C(C)(O)C=C LBRDQQPGFNRZGV-UHFFFAOYSA-N 0.000 claims 3
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 claims 3
- WLADCPLMVBLPJO-UHFFFAOYSA-N 4-chloro-2-methylbut-2-enal Chemical compound O=CC(C)=CCCl WLADCPLMVBLPJO-UHFFFAOYSA-N 0.000 claims 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 239000003054 catalyst Substances 0.000 claims 3
- 239000012259 ether extract Substances 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 3
- 230000007935 neutral effect Effects 0.000 claims 3
- 150000004714 phosphonium salts Chemical class 0.000 claims 3
- 229910052698 phosphorus Inorganic materials 0.000 claims 3
- 238000010992 reflux Methods 0.000 claims 3
- LHMZSNPBAJFHNR-UHFFFAOYSA-M (2,4-dimethoxy-3,6-dimethylphenyl)methyl-triphenylphosphanium;chloride Chemical compound [Cl-].COC1=C(C)C(OC)=CC(C)=C1C[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 LHMZSNPBAJFHNR-UHFFFAOYSA-M 0.000 claims 2
- DGDDTOWTALANOE-UHFFFAOYSA-N 1,3-dichloro-2-(chloromethyl)-5-methoxybenzene Chemical compound COC1=CC(Cl)=C(CCl)C(Cl)=C1 DGDDTOWTALANOE-UHFFFAOYSA-N 0.000 claims 2
- SSNXYMVLSOMJLU-UHFFFAOYSA-N 1,3-dichloro-5-methoxybenzene Chemical compound COC1=CC(Cl)=CC(Cl)=C1 SSNXYMVLSOMJLU-UHFFFAOYSA-N 0.000 claims 2
- UMYYXIIJWNIOPI-UHFFFAOYSA-N 1-methoxy-2,3-dimethyl-5-nitrobenzene Chemical compound COC1=CC([N+]([O-])=O)=CC(C)=C1C UMYYXIIJWNIOPI-UHFFFAOYSA-N 0.000 claims 2
- RSRLXRIHUGVPDS-UHFFFAOYSA-N 2,3-dimethyl-5-nitroaniline Chemical compound CC1=CC([N+]([O-])=O)=CC(N)=C1C RSRLXRIHUGVPDS-UHFFFAOYSA-N 0.000 claims 2
- GQVYCDUMNSPVOD-UHFFFAOYSA-N 2,3-dimethyl-5-nitrophenol Chemical compound CC1=CC([N+]([O-])=O)=CC(O)=C1C GQVYCDUMNSPVOD-UHFFFAOYSA-N 0.000 claims 2
- WCDVUDDKKZGHFN-UHFFFAOYSA-N 3-chloro-2,5,6-trimethylaniline Chemical compound CC1=CC(Cl)=C(C)C(N)=C1C WCDVUDDKKZGHFN-UHFFFAOYSA-N 0.000 claims 2
- AGNSRKFKYVFXLG-UHFFFAOYSA-N 3-chloro-2,5-dimethylphenol Chemical compound CC1=CC(O)=C(C)C(Cl)=C1 AGNSRKFKYVFXLG-UHFFFAOYSA-N 0.000 claims 2
- MFITYIKFSYHAQN-UHFFFAOYSA-N 3-methoxy-4,5-dimethylaniline Chemical compound COC1=CC(N)=CC(C)=C1C MFITYIKFSYHAQN-UHFFFAOYSA-N 0.000 claims 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 2
- AIJULSRZWUXGPQ-UHFFFAOYSA-N Methylglyoxal Chemical compound CC(=O)C=O AIJULSRZWUXGPQ-UHFFFAOYSA-N 0.000 claims 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 2
- 229960000583 acetic acid Drugs 0.000 claims 2
- 150000001299 aldehydes Chemical class 0.000 claims 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- SPWVRYZQLGQKGK-UHFFFAOYSA-N dichloromethane;hexane Chemical compound ClCCl.CCCCCC SPWVRYZQLGQKGK-UHFFFAOYSA-N 0.000 claims 2
- 238000004821 distillation Methods 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 2
- 150000002431 hydrogen Chemical group 0.000 claims 2
- 238000005984 hydrogenation reaction Methods 0.000 claims 2
- 238000002955 isolation Methods 0.000 claims 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 239000003208 petroleum Substances 0.000 claims 2
- 239000012071 phase Substances 0.000 claims 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 2
- 229910052708 sodium Inorganic materials 0.000 claims 2
- 239000011734 sodium Substances 0.000 claims 2
- 239000011780 sodium chloride Substances 0.000 claims 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
- RMPAEBJCZAEVGB-UHFFFAOYSA-M (2-chloro-4-methoxy-3,5,6-trimethylphenyl)methyl-triphenylphosphanium;chloride Chemical compound [Cl-].ClC1=C(C)C(OC)=C(C)C(C)=C1C[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 RMPAEBJCZAEVGB-UHFFFAOYSA-M 0.000 claims 1
- CYWRGEADBSVITR-UHFFFAOYSA-M (6-chloro-4-methoxy-2,3-dimethylphenyl)methyl-triphenylphosphanium;chloride Chemical compound [Cl-].CC1=C(C)C(OC)=CC(Cl)=C1C[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 CYWRGEADBSVITR-UHFFFAOYSA-M 0.000 claims 1
- JWNIPXFYDYWGQT-UHFFFAOYSA-N 1,3,4-trichloro-2-(chloromethyl)-5-methoxybenzene Chemical compound COC1=CC(Cl)=C(CCl)C(Cl)=C1Cl JWNIPXFYDYWGQT-UHFFFAOYSA-N 0.000 claims 1
- GIUXLBFXMAOOQJ-UHFFFAOYSA-N 1,3-dimethoxy-2,5-dimethylbenzene Chemical group COC1=CC(C)=CC(OC)=C1C GIUXLBFXMAOOQJ-UHFFFAOYSA-N 0.000 claims 1
- KTHSXIDIBJLTIB-UHFFFAOYSA-N 1-(2-chloropropan-2-yl)-2-methylbenzene Chemical compound CC1=CC=CC=C1C(C)(C)Cl KTHSXIDIBJLTIB-UHFFFAOYSA-N 0.000 claims 1
- SQNHUULDEHMUBE-UHFFFAOYSA-N 1-chloro-2,4,5-trimethyl-3-nitrobenzene Chemical compound CC1=CC(Cl)=C(C)C([N+]([O-])=O)=C1C SQNHUULDEHMUBE-UHFFFAOYSA-N 0.000 claims 1
- LJQDRBHJSRPHEP-UHFFFAOYSA-N 1-chloro-2,4,5-trimethylbenzene Chemical compound CC1=CC(C)=C(Cl)C=C1C LJQDRBHJSRPHEP-UHFFFAOYSA-N 0.000 claims 1
- ICVFACWRHDRTIM-UHFFFAOYSA-N 1-chloro-2,5-dimethyl-3-nitrobenzene Chemical compound CC1=CC(Cl)=C(C)C([N+]([O-])=O)=C1 ICVFACWRHDRTIM-UHFFFAOYSA-N 0.000 claims 1
- WWAJFOUPOXEVPB-UHFFFAOYSA-N 1-chloro-3-methoxy-2,4,5-trimethylbenzene Chemical compound COC1=C(C)C(C)=CC(Cl)=C1C WWAJFOUPOXEVPB-UHFFFAOYSA-N 0.000 claims 1
- GGCMNCCMYGTHTO-UHFFFAOYSA-N 1-chloro-5-(chloromethyl)-2,4-dimethylbenzene Chemical compound CC1=CC(C)=C(CCl)C=C1Cl GGCMNCCMYGTHTO-UHFFFAOYSA-N 0.000 claims 1
- WWGQHTJIFOQAOC-UHFFFAOYSA-N 2,3,5-trichlorophenol Chemical compound OC1=CC(Cl)=CC(Cl)=C1Cl WWGQHTJIFOQAOC-UHFFFAOYSA-N 0.000 claims 1
- VVAKEQGKZNKUSU-UHFFFAOYSA-N 2,3-dimethylaniline Chemical compound CC1=CC=CC(N)=C1C VVAKEQGKZNKUSU-UHFFFAOYSA-N 0.000 claims 1
- VOYUCTPCAWSYTF-UHFFFAOYSA-N 2,6-dichloro-4-methoxybenzaldehyde Chemical compound COC1=CC(Cl)=C(C=O)C(Cl)=C1 VOYUCTPCAWSYTF-UHFFFAOYSA-N 0.000 claims 1
- ALJZUSDCIRVOFI-UHFFFAOYSA-N 3-chloro-2,5,6-trimethylphenol Chemical compound CC1=CC(Cl)=C(C)C(O)=C1C ALJZUSDCIRVOFI-UHFFFAOYSA-N 0.000 claims 1
- QYAKLJJTQHCHLJ-UHFFFAOYSA-N 3-chloro-2,5-dimethylaniline Chemical compound CC1=CC(N)=C(C)C(Cl)=C1 QYAKLJJTQHCHLJ-UHFFFAOYSA-N 0.000 claims 1
- VLRGXXKFHVJQOL-UHFFFAOYSA-N 3-chloropentane-2,4-dione Chemical compound CC(=O)C(Cl)C(C)=O VLRGXXKFHVJQOL-UHFFFAOYSA-N 0.000 claims 1
- HTLCSEOPJNXFSJ-UHFFFAOYSA-N 3-methyl-2-phenylpenta-2,4-dienal Chemical compound C1(=CC=CC=C1)C(C=O)=C(C=C)C HTLCSEOPJNXFSJ-UHFFFAOYSA-N 0.000 claims 1
- LGPCPFNWVGOQDB-UHFFFAOYSA-N 4-(chloromethyl)-1,3-dimethoxy-2,5-dimethylbenzene Chemical compound COC1=CC(C)=C(CCl)C(OC)=C1C LGPCPFNWVGOQDB-UHFFFAOYSA-N 0.000 claims 1
- JLLYLQLDYORLBB-UHFFFAOYSA-N 5-bromo-n-methylthiophene-2-sulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(Br)S1 JLLYLQLDYORLBB-UHFFFAOYSA-N 0.000 claims 1
- GHMROWFWYDPHBF-UHFFFAOYSA-N 5-fluoro-1-methoxy-2,3-dimethylbenzene Chemical compound COC1=CC(F)=CC(C)=C1C GHMROWFWYDPHBF-UHFFFAOYSA-N 0.000 claims 1
- POXUBCRWADVFBX-UHFFFAOYSA-N 5-methoxy-5,6-dimethylcyclohexa-1,3-diene Chemical compound COC1(C)C=CC=CC1C POXUBCRWADVFBX-UHFFFAOYSA-N 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 1
- YNPXMLHRQLVRGE-UHFFFAOYSA-N CC1=C(C(=C(C=C1OC)Br)CCl)C Chemical compound CC1=C(C(=C(C=C1OC)Br)CCl)C YNPXMLHRQLVRGE-UHFFFAOYSA-N 0.000 claims 1
- KSSTYLKXOXKJFW-UHFFFAOYSA-N CC1=C(C(=C(C=C1OC)F)CCl)C Chemical compound CC1=C(C(=C(C=C1OC)F)CCl)C KSSTYLKXOXKJFW-UHFFFAOYSA-N 0.000 claims 1
- HFMPNQNXRIJQRS-UHFFFAOYSA-M COC(C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)(C1Cl)C(Cl)=CC=C1Cl.[Cl-] Chemical compound COC(C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)(C1Cl)C(Cl)=CC=C1Cl.[Cl-] HFMPNQNXRIJQRS-UHFFFAOYSA-M 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 241000790917 Dioxys <bee> Species 0.000 claims 1
- 206010072063 Exposure to lead Diseases 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims 1
- 238000007239 Wittig reaction Methods 0.000 claims 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 1
- 238000013019 agitation Methods 0.000 claims 1
- 230000001476 alcoholic effect Effects 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 150000001336 alkenes Chemical class 0.000 claims 1
- 125000001118 alkylidene group Chemical group 0.000 claims 1
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- 150000001450 anions Chemical class 0.000 claims 1
- 239000008346 aqueous phase Substances 0.000 claims 1
- 239000002585 base Substances 0.000 claims 1
- SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 239000001569 carbon dioxide Substances 0.000 claims 1
- 229910002092 carbon dioxide Inorganic materials 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 238000009833 condensation Methods 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- 229960004698 dichlorobenzyl alcohol Drugs 0.000 claims 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims 1
- 238000001035 drying Methods 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- YLFXEUMFBVGYEL-XQRVVYSFSA-N ethyl (z)-3-methyl-4-oxobut-2-enoate Chemical compound CCOC(=O)\C=C(\C)C=O YLFXEUMFBVGYEL-XQRVVYSFSA-N 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 239000007789 gas Substances 0.000 claims 1
- 239000012362 glacial acetic acid Substances 0.000 claims 1
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical class OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims 1
- 239000005457 ice water Substances 0.000 claims 1
- MVFCKEFYUDZOCX-UHFFFAOYSA-N iron(2+);dinitrate Chemical compound [Fe+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O MVFCKEFYUDZOCX-UHFFFAOYSA-N 0.000 claims 1
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 claims 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- JEHCHYAKAXDFKV-UHFFFAOYSA-J lead tetraacetate Chemical compound CC(=O)O[Pb](OC(C)=O)(OC(C)=O)OC(C)=O JEHCHYAKAXDFKV-UHFFFAOYSA-J 0.000 claims 1
- 239000012280 lithium aluminium hydride Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000002844 melting Methods 0.000 claims 1
- 230000008018 melting Effects 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 229910052987 metal hydride Inorganic materials 0.000 claims 1
- 150000004681 metal hydrides Chemical class 0.000 claims 1
- 150000004706 metal oxides Chemical class 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 238000005648 named reaction Methods 0.000 claims 1
- 229910052759 nickel Inorganic materials 0.000 claims 1
- 229910017604 nitric acid Inorganic materials 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 239000012299 nitrogen atmosphere Substances 0.000 claims 1
- OIPPWFOQEKKFEE-UHFFFAOYSA-N orcinol Chemical compound CC1=CC(O)=CC(O)=C1 OIPPWFOQEKKFEE-UHFFFAOYSA-N 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- 239000012074 organic phase Substances 0.000 claims 1
- 238000007248 oxidative elimination reaction Methods 0.000 claims 1
- 229910052763 palladium Inorganic materials 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 239000011574 phosphorus Substances 0.000 claims 1
- 239000002574 poison Substances 0.000 claims 1
- 231100000614 poison Toxicity 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 238000007670 refining Methods 0.000 claims 1
- 238000007127 saponification reaction Methods 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 229910000077 silane Inorganic materials 0.000 claims 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims 1
- 235000010288 sodium nitrite Nutrition 0.000 claims 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 claims 1
- 235000019345 sodium thiosulphate Nutrition 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 235000002906 tartaric acid Nutrition 0.000 claims 1
- 239000011975 tartaric acid Substances 0.000 claims 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 claims 1
- GGUBFICZYGKNTD-UHFFFAOYSA-N triethyl phosphonoacetate Chemical compound CCOC(=O)CP(=O)(OCC)OCC GGUBFICZYGKNTD-UHFFFAOYSA-N 0.000 claims 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 claims 1
- KIEGHZZLKDAUPX-UHFFFAOYSA-M triphenyl-[(2,3,6-trichloro-4-methoxyphenyl)methyl]phosphanium;chloride Chemical compound [Cl-].ClC1=C(Cl)C(OC)=CC(Cl)=C1C[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 KIEGHZZLKDAUPX-UHFFFAOYSA-M 0.000 claims 1
- IIHPVYJPDKJYOU-UHFFFAOYSA-N triphenylcarbethoxymethylenephosphorane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CC(=O)OCC)C1=CC=CC=C1 IIHPVYJPDKJYOU-UHFFFAOYSA-N 0.000 claims 1
- 235000013522 vodka Nutrition 0.000 claims 1
- 238000005406 washing Methods 0.000 claims 1
- 229910052725 zinc Inorganic materials 0.000 claims 1
- 239000011701 zinc Substances 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/54—Quaternary phosphonium compounds
- C07F9/5456—Arylalkanephosphonium compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/23—Preparation of halogenated hydrocarbons by dehalogenation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/07—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms
- C07C205/11—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms having nitro groups bound to carbon atoms of six-membered aromatic rings
- C07C205/12—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms having nitro groups bound to carbon atoms of six-membered aromatic rings the six-membered aromatic ring or a condensed ring system containing that ring being substituted by halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/13—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups
- C07C205/20—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups having nitro groups and hydroxy groups bound to carbon atoms of six-membered aromatic rings
- C07C205/21—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups having nitro groups and hydroxy groups bound to carbon atoms of six-membered aromatic rings having nitro groups and hydroxy groups bound to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C205/22—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups having nitro groups and hydroxy groups bound to carbon atoms of six-membered aromatic rings having nitro groups and hydroxy groups bound to carbon atoms of the same non-condensed six-membered aromatic ring having one nitro groups bound to the ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/27—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups
- C07C205/35—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/36—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system
- C07C205/37—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/01—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
- C07C37/045—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis by substitution of a group bound to the ring by nitrogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/16—Preparation of ethers by reaction of esters of mineral or organic acids with hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/30—Preparation of ethers by reactions not forming ether-oxygen bonds by increasing the number of carbon atoms, e.g. by oligomerisation
-
- 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
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
- C07C45/515—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an acetalised, ketalised hemi-acetalised, or hemi-ketalised hydroxyl group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Immunology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Dermatology (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH1303274A CH605562A5 (no) | 1974-09-26 | 1974-09-26 |
Publications (1)
Publication Number | Publication Date |
---|---|
SU623515A3 true SU623515A3 (ru) | 1978-09-05 |
Family
ID=4388688
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
SU752178997A SU623515A3 (ru) | 1974-09-26 | 1975-09-25 | Способ получени полиеновых соединений или их солей |
Country Status (22)
Country | Link |
---|---|
JP (1) | JPS5951531B2 (no) |
AR (1) | AR212858A1 (no) |
AT (1) | AT346311B (no) |
BE (1) | BE833784A (no) |
BR (1) | BR7506154A (no) |
CA (1) | CA1050042A (no) |
CH (1) | CH605562A5 (no) |
CU (1) | CU34345A (no) |
DD (1) | DD122072A5 (no) |
DE (1) | DE2542612A1 (no) |
FR (1) | FR2285864B1 (no) |
GB (1) | GB1514975A (no) |
HU (1) | HU172958B (no) |
IE (1) | IE41801B1 (no) |
IL (1) | IL47929A (no) |
LU (1) | LU73452A1 (no) |
NL (1) | NL177913C (no) |
NZ (1) | NZ178425A (no) |
PH (1) | PH12883A (no) |
SU (1) | SU623515A3 (no) |
YU (1) | YU40124B (no) |
ZA (1) | ZA755208B (no) |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4395575A (en) | 1975-11-14 | 1983-07-26 | Hoffmann-La Roche, Inc. | 5(Halophenyl)-2-fluoro-pentadienals |
US4321209A (en) | 1975-11-14 | 1982-03-23 | Hoffmann-La Roche Inc. | Fluorinated aromatic polyenes |
US4335248A (en) | 1975-11-14 | 1982-06-15 | Hoffmann-La Roche Inc. | Fluorinated polyenes |
US4338253A (en) | 1975-11-14 | 1982-07-06 | Hoffmann-La Roche Inc. | Fluorinated aromatic polyenes |
US4266073A (en) * | 1975-11-14 | 1981-05-05 | Hoffmann-La Roche Inc. | Fluorinated aromatic polyenes |
US4375563A (en) | 1975-11-14 | 1983-03-01 | Hoffmann-La Roche Inc. | Fluorinated aromatic polyenes |
US4201727A (en) | 1976-11-14 | 1980-05-06 | Hoffmann-La Roche Inc. | Fluorinated aromatic polyenes |
US4299995A (en) | 1979-05-10 | 1981-11-10 | Hoffmann-La Roche Inc. | Fluorinated polyenes |
CA1111441A (en) | 1976-12-20 | 1981-10-27 | Werner Bollag | Polyene compounds |
US4200647A (en) * | 1977-12-21 | 1980-04-29 | Hoffmann-La Roche Inc. | Vitamin A compositions to treat rheumatic disease |
US4642318A (en) * | 1982-11-17 | 1987-02-10 | Klaus Wolff | Method for decreasing radiation load in PUVA therapy |
ZA854828B (en) * | 1984-07-27 | 1986-03-26 | Hoffmann La Roche | Phenyl nonatetraenoic acid derivatives |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1109671B (de) * | 1958-10-17 | 1961-06-29 | Basf Ag | Verfahren zur Herstellung von ª‡,ª‰-ungesaettigten Carbonsaeureestern oder der freien Saeuren |
-
1974
- 1974-09-26 CH CH1303274A patent/CH605562A5/xx not_active IP Right Cessation
-
1975
- 1975-08-13 ZA ZA00755208A patent/ZA755208B/xx unknown
- 1975-08-15 IL IL47929A patent/IL47929A/xx unknown
- 1975-08-19 NZ NZ178425A patent/NZ178425A/xx unknown
- 1975-08-26 CA CA234,206A patent/CA1050042A/en not_active Expired
- 1975-09-10 YU YU2287/75A patent/YU40124B/xx unknown
- 1975-09-12 NL NLAANVRAGE7510778,A patent/NL177913C/xx not_active IP Right Cessation
- 1975-09-12 AR AR260364A patent/AR212858A1/es active
- 1975-09-16 PH PH17579A patent/PH12883A/en unknown
- 1975-09-18 CU CU7534345A patent/CU34345A/es unknown
- 1975-09-23 JP JP50114373A patent/JPS5951531B2/ja not_active Expired
- 1975-09-24 LU LU73452A patent/LU73452A1/xx unknown
- 1975-09-24 DE DE19752542612 patent/DE2542612A1/de active Granted
- 1975-09-24 HU HU75HO00001839A patent/HU172958B/hu unknown
- 1975-09-24 FR FR7529226A patent/FR2285864B1/fr not_active Expired
- 1975-09-24 BR BR7506154*A patent/BR7506154A/pt unknown
- 1975-09-25 AT AT734775A patent/AT346311B/de not_active IP Right Cessation
- 1975-09-25 IE IE2098/75A patent/IE41801B1/en unknown
- 1975-09-25 BE BE160342A patent/BE833784A/xx not_active IP Right Cessation
- 1975-09-25 SU SU752178997A patent/SU623515A3/ru active
- 1975-09-25 DD DD188555A patent/DD122072A5/xx unknown
- 1975-09-26 GB GB39545/75A patent/GB1514975A/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
YU40124B (en) | 1985-08-31 |
IE41801L (en) | 1976-03-26 |
JPS5951531B2 (ja) | 1984-12-14 |
AR212858A1 (es) | 1978-10-31 |
AT346311B (de) | 1978-11-10 |
LU73452A1 (no) | 1977-05-16 |
JPS51125233A (en) | 1976-11-01 |
NL177913C (nl) | 1985-12-16 |
BR7506154A (pt) | 1976-08-03 |
IE41801B1 (en) | 1980-03-26 |
YU228775A (en) | 1983-01-21 |
DE2542612A1 (de) | 1976-04-22 |
ATA734775A (de) | 1978-03-15 |
NZ178425A (en) | 1978-03-06 |
IL47929A0 (en) | 1975-11-25 |
FR2285864B1 (fr) | 1980-03-28 |
HU172958B (hu) | 1979-01-28 |
DD122072A5 (no) | 1976-09-12 |
CA1050042A (en) | 1979-03-06 |
BE833784A (fr) | 1976-03-25 |
IL47929A (en) | 1978-07-31 |
DE2542612C2 (no) | 1987-09-10 |
FR2285864A1 (fr) | 1976-04-23 |
NL7510778A (nl) | 1976-03-30 |
AU8418775A (en) | 1977-02-24 |
CU34345A (es) | 1979-09-08 |
GB1514975A (en) | 1978-06-21 |
PH12883A (en) | 1979-09-28 |
ZA755208B (en) | 1976-07-28 |
CH605562A5 (no) | 1978-09-29 |
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