NO330857B1 - Fremgangsmate for a fremstille 1-acetoksy-3-(substituert fenyl)propen-forbindelse. - Google Patents
Fremgangsmate for a fremstille 1-acetoksy-3-(substituert fenyl)propen-forbindelse. Download PDFInfo
- Publication number
- NO330857B1 NO330857B1 NO20053261A NO20053261A NO330857B1 NO 330857 B1 NO330857 B1 NO 330857B1 NO 20053261 A NO20053261 A NO 20053261A NO 20053261 A NO20053261 A NO 20053261A NO 330857 B1 NO330857 B1 NO 330857B1
- Authority
- NO
- Norway
- Prior art keywords
- acetoxy
- propene
- substituted phenyl
- group
- preparing
- Prior art date
Links
- -1 1-acetoxy-3- (substituted phenyl) propylene compound Chemical class 0.000 title claims description 59
- 238000000034 method Methods 0.000 title claims description 59
- 238000002360 preparation method Methods 0.000 title description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 6
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 69
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 56
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 47
- 239000007789 gas Substances 0.000 claims description 32
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 claims description 30
- QFXJBPCTHSTOPE-UHFFFAOYSA-N methacrolein diacetate Chemical compound CC(=O)OC(C(C)=C)OC(C)=O QFXJBPCTHSTOPE-UHFFFAOYSA-N 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 26
- 239000003054 catalyst Substances 0.000 claims description 24
- 150000002366 halogen compounds Chemical class 0.000 claims description 22
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical class FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 17
- 238000004519 manufacturing process Methods 0.000 claims description 17
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 15
- 125000002070 alkenylidene group Chemical group 0.000 claims description 14
- ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 claims description 14
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 14
- 150000008648 triflates Chemical class 0.000 claims description 12
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 11
- 229910052796 boron Inorganic materials 0.000 claims description 11
- 230000000737 periodic effect Effects 0.000 claims description 11
- OHBQPCCCRFSCAX-UHFFFAOYSA-N 1,4-Dimethoxybenzene Chemical compound COC1=CC=C(OC)C=C1 OHBQPCCCRFSCAX-UHFFFAOYSA-N 0.000 claims description 10
- 229910015900 BF3 Inorganic materials 0.000 claims description 9
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 8
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims description 8
- 229910052718 tin Inorganic materials 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 235000005074 zinc chloride Nutrition 0.000 claims description 7
- 239000011592 zinc chloride Substances 0.000 claims description 7
- CRUILBNAQILVHZ-UHFFFAOYSA-N 1,2,3-trimethoxybenzene Chemical compound COC1=CC=CC(OC)=C1OC CRUILBNAQILVHZ-UHFFFAOYSA-N 0.000 claims description 6
- AMMSPBQAQKIQPO-UHFFFAOYSA-N [3-(3,4-dimethoxyphenyl)-2-methylprop-1-enyl] acetate Chemical compound COC1=CC=C(CC(C)=COC(C)=O)C=C1OC AMMSPBQAQKIQPO-UHFFFAOYSA-N 0.000 claims description 6
- 150000001555 benzenes Chemical class 0.000 claims description 6
- KPWJBEFBFLRCLH-UHFFFAOYSA-L cadmium bromide Chemical compound Br[Cd]Br KPWJBEFBFLRCLH-UHFFFAOYSA-L 0.000 claims description 6
- YKYOUMDCQGMQQO-UHFFFAOYSA-L cadmium dichloride Chemical compound Cl[Cd]Cl YKYOUMDCQGMQQO-UHFFFAOYSA-L 0.000 claims description 6
- OKIIEJOIXGHUKX-UHFFFAOYSA-L cadmium iodide Chemical compound [Cd+2].[I-].[I-] OKIIEJOIXGHUKX-UHFFFAOYSA-L 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 229910052747 lanthanoid Inorganic materials 0.000 claims description 6
- 150000002602 lanthanoids Chemical class 0.000 claims description 6
- VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 claims description 6
- BHHYHSUAOQUXJK-UHFFFAOYSA-L zinc fluoride Chemical compound F[Zn]F BHHYHSUAOQUXJK-UHFFFAOYSA-L 0.000 claims description 6
- UAYWVJHJZHQCIE-UHFFFAOYSA-L zinc iodide Chemical compound I[Zn]I UAYWVJHJZHQCIE-UHFFFAOYSA-L 0.000 claims description 6
- SBTSVTLGWRLWOD-UHFFFAOYSA-L copper(ii) triflate Chemical compound [Cu+2].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F SBTSVTLGWRLWOD-UHFFFAOYSA-L 0.000 claims description 5
- LVZGQWKTUCVPBQ-UHFFFAOYSA-N acetic acid;trifluoroborane Chemical compound CC(O)=O.FB(F)F LVZGQWKTUCVPBQ-UHFFFAOYSA-N 0.000 claims description 4
- BNBQRQQYDMDJAH-UHFFFAOYSA-N benzodioxan Chemical compound C1=CC=C2OCCOC2=C1 BNBQRQQYDMDJAH-UHFFFAOYSA-N 0.000 claims description 4
- MBXZLESDQNKPPV-UHFFFAOYSA-N (1-acetyloxy-2-methylidenebutyl) acetate Chemical compound CCC(=C)C(OC(C)=O)OC(C)=O MBXZLESDQNKPPV-UHFFFAOYSA-N 0.000 claims description 3
- YCFKSMMNWNLDMR-UHFFFAOYSA-N (1-acetyloxy-2-methylpent-2-enyl) acetate Chemical compound CCC=C(C)C(OC(C)=O)OC(C)=O YCFKSMMNWNLDMR-UHFFFAOYSA-N 0.000 claims description 3
- AGIQIOSHSMJYJP-UHFFFAOYSA-N 1,2,4-Trimethoxybenzene Chemical compound COC1=CC=C(OC)C(OC)=C1 AGIQIOSHSMJYJP-UHFFFAOYSA-N 0.000 claims description 3
- YSKRCULMSHXOLA-UHFFFAOYSA-N 1-acetyloxybut-2-enyl acetate Chemical compound CC=CC(OC(C)=O)OC(C)=O YSKRCULMSHXOLA-UHFFFAOYSA-N 0.000 claims description 3
- OJGOLJMFDQVUHX-UHFFFAOYSA-N 1-acetyloxypent-2-enyl acetate Chemical compound CCC=CC(OC(C)=O)OC(C)=O OJGOLJMFDQVUHX-UHFFFAOYSA-N 0.000 claims description 3
- TXECTBGVEUDNSL-UHFFFAOYSA-N 1-acetyloxyprop-2-enyl acetate Chemical compound CC(=O)OC(C=C)OC(C)=O TXECTBGVEUDNSL-UHFFFAOYSA-N 0.000 claims description 3
- LVEULQCPJDDSLD-UHFFFAOYSA-L cadmium fluoride Chemical compound F[Cd]F LVEULQCPJDDSLD-UHFFFAOYSA-L 0.000 claims description 3
- 229940075417 cadmium iodide Drugs 0.000 claims description 3
- 229960002523 mercuric chloride Drugs 0.000 claims description 3
- 229960003671 mercuric iodide Drugs 0.000 claims description 3
- NGYIMTKLQULBOO-UHFFFAOYSA-L mercury dibromide Chemical compound Br[Hg]Br NGYIMTKLQULBOO-UHFFFAOYSA-L 0.000 claims description 3
- LWJROJCJINYWOX-UHFFFAOYSA-L mercury dichloride Chemical compound Cl[Hg]Cl LWJROJCJINYWOX-UHFFFAOYSA-L 0.000 claims description 3
- YFDLHELOZYVNJE-UHFFFAOYSA-L mercury diiodide Chemical compound I[Hg]I YFDLHELOZYVNJE-UHFFFAOYSA-L 0.000 claims description 3
- CHNLPLHJUPMEOI-UHFFFAOYSA-N oxolane;trifluoroborane Chemical class FB(F)F.C1CCOC1 CHNLPLHJUPMEOI-UHFFFAOYSA-N 0.000 claims description 3
- QRUBYZBWAOOHSV-UHFFFAOYSA-M silver trifluoromethanesulfonate Chemical compound [Ag+].[O-]S(=O)(=O)C(F)(F)F QRUBYZBWAOOHSV-UHFFFAOYSA-M 0.000 claims description 3
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 3
- MJCYPBSRKLJZTB-UHFFFAOYSA-N trifluoroborane;dihydrate Chemical compound O.O.FB(F)F MJCYPBSRKLJZTB-UHFFFAOYSA-N 0.000 claims description 3
- 229940102001 zinc bromide Drugs 0.000 claims description 3
- 229910052684 Cerium Inorganic materials 0.000 claims description 2
- 229910052692 Dysprosium Inorganic materials 0.000 claims description 2
- 229910052691 Erbium Inorganic materials 0.000 claims description 2
- 229910052689 Holmium Inorganic materials 0.000 claims description 2
- 229910052765 Lutetium Inorganic materials 0.000 claims description 2
- 229910052775 Thulium Inorganic materials 0.000 claims description 2
- 229910052769 Ytterbium Inorganic materials 0.000 claims description 2
- 150000001649 bromium compounds Chemical class 0.000 claims description 2
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- FMSYTQMJOCCCQS-UHFFFAOYSA-L difluoromercury Chemical compound F[Hg]F FMSYTQMJOCCCQS-UHFFFAOYSA-L 0.000 claims description 2
- KBQHZAAAGSGFKK-UHFFFAOYSA-N dysprosium atom Chemical compound [Dy] KBQHZAAAGSGFKK-UHFFFAOYSA-N 0.000 claims description 2
- UYAHIZSMUZPPFV-UHFFFAOYSA-N erbium Chemical compound [Er] UYAHIZSMUZPPFV-UHFFFAOYSA-N 0.000 claims description 2
- 150000002222 fluorine compounds Chemical class 0.000 claims description 2
- KJZYNXUDTRRSPN-UHFFFAOYSA-N holmium atom Chemical compound [Ho] KJZYNXUDTRRSPN-UHFFFAOYSA-N 0.000 claims description 2
- OHSVLFRHMCKCQY-UHFFFAOYSA-N lutetium atom Chemical compound [Lu] OHSVLFRHMCKCQY-UHFFFAOYSA-N 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims 1
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 abstract description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract description 2
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 150000002989 phenols Chemical class 0.000 abstract 1
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 54
- 239000000203 mixture Substances 0.000 description 53
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 42
- 239000012295 chemical reaction liquid Substances 0.000 description 39
- 229910052786 argon Inorganic materials 0.000 description 27
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 238000004128 high performance liquid chromatography Methods 0.000 description 22
- OYUNCLNMRZPSCZ-UHFFFAOYSA-N [3-(1,3-benzodioxol-5-yl)-2-methylprop-1-enyl] acetate Chemical compound CC(=O)OC=C(C)CC1=CC=C2OCOC2=C1 OYUNCLNMRZPSCZ-UHFFFAOYSA-N 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 13
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
- 239000011259 mixed solution Substances 0.000 description 8
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 8
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical class FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 7
- 238000004821 distillation Methods 0.000 description 7
- AHZJKOKFZJYCLG-UHFFFAOYSA-K trifluoromethanesulfonate;ytterbium(3+) Chemical compound [Yb+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F AHZJKOKFZJYCLG-UHFFFAOYSA-K 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- UNOOQQABDFYORN-UHFFFAOYSA-N [3-(4-methoxyphenyl)-2-methylprop-1-enyl] acetate Chemical compound COC1=CC=C(CC(C)=COC(C)=O)C=C1 UNOOQQABDFYORN-UHFFFAOYSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 238000011088 calibration curve Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical compound CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 description 4
- YGYWFKSHKQCIPX-UHFFFAOYSA-N [3-(2,5-dimethoxyphenyl)-2-methylprop-1-enyl] acetate Chemical compound COC1=CC=C(OC)C(CC(C)=COC(C)=O)=C1 YGYWFKSHKQCIPX-UHFFFAOYSA-N 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 239000002841 Lewis acid Substances 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- OFRIWRBUNPHNMD-UHFFFAOYSA-N [3-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-methylprop-1-enyl] acetate Chemical compound O1CCOC2=CC(CC(C)=COC(=O)C)=CC=C21 OFRIWRBUNPHNMD-UHFFFAOYSA-N 0.000 description 3
- 239000003905 agrochemical Substances 0.000 description 3
- PHSMPGGNMIPKTH-UHFFFAOYSA-K cerium(3+);trifluoromethanesulfonate Chemical compound [Ce+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F PHSMPGGNMIPKTH-UHFFFAOYSA-K 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- GLQOFBCJADYRKR-UHFFFAOYSA-K erbium(3+);trifluoromethanesulfonate Chemical compound [Er+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F GLQOFBCJADYRKR-UHFFFAOYSA-K 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 150000007517 lewis acids Chemical class 0.000 description 3
- NRMNRSCGHRWJAK-UHFFFAOYSA-K lutetium(3+);trifluoromethanesulfonate Chemical compound [Lu+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F NRMNRSCGHRWJAK-UHFFFAOYSA-K 0.000 description 3
- 239000002304 perfume Substances 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- PBASUZORNBYVFM-UHFFFAOYSA-K thulium(3+);trifluoromethanesulfonate Chemical compound [Tm+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F PBASUZORNBYVFM-UHFFFAOYSA-K 0.000 description 3
- HIAIVILTZQDDNY-UHFFFAOYSA-J tin(4+);trifluoromethanesulfonate Chemical compound [Sn+4].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F HIAIVILTZQDDNY-UHFFFAOYSA-J 0.000 description 3
- CKLHRQNQYIJFFX-UHFFFAOYSA-K ytterbium(III) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Yb+3] CKLHRQNQYIJFFX-UHFFFAOYSA-K 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 244000309464 bull Species 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 2
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- DBPDCYACEYLEMY-UHFFFAOYSA-K holmium(3+);trifluoromethanesulfonate Chemical compound [Ho+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F DBPDCYACEYLEMY-UHFFFAOYSA-K 0.000 description 2
- 239000012263 liquid product Substances 0.000 description 2
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 description 2
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 2
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 1
- MAYVZUQEFSJDHA-UHFFFAOYSA-N 1,5-bis(methylsulfanyl)naphthalene Chemical compound C1=CC=C2C(SC)=CC=CC2=C1SC MAYVZUQEFSJDHA-UHFFFAOYSA-N 0.000 description 1
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 1
- APFWLFUGBMRXCS-UHFFFAOYSA-N 4,7-dihydroxy-3-phenylchromen-2-one Chemical compound O=C1OC2=CC(O)=CC=C2C(O)=C1C1=CC=CC=C1 APFWLFUGBMRXCS-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- GQKYKPLGNBXERW-UHFFFAOYSA-N 6-fluoro-1h-indazol-5-amine Chemical compound C1=C(F)C(N)=CC2=C1NN=C2 GQKYKPLGNBXERW-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- DFFGXGLKNGYGOY-UHFFFAOYSA-N [3-(4-tert-butylphenyl)-2-methylprop-1-enyl] acetate Chemical compound CC(=O)OC=C(C)CC1=CC=C(C(C)(C)C)C=C1 DFFGXGLKNGYGOY-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000005530 alkylenedioxy group Chemical group 0.000 description 1
- 125000001118 alkylidene group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- OKOSPWNNXVDXKZ-UHFFFAOYSA-N but-3-enoyl chloride Chemical compound ClC(=O)CC=C OKOSPWNNXVDXKZ-UHFFFAOYSA-N 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- VYLVYHXQOHJDJL-UHFFFAOYSA-K cerium trichloride Chemical compound Cl[Ce](Cl)Cl VYLVYHXQOHJDJL-UHFFFAOYSA-K 0.000 description 1
- QCCDYNYSHILRDG-UHFFFAOYSA-K cerium(3+);trifluoride Chemical compound [F-].[F-].[F-].[Ce+3] QCCDYNYSHILRDG-UHFFFAOYSA-K 0.000 description 1
- ZEDZJUDTPVFRNB-UHFFFAOYSA-K cerium(3+);triiodide Chemical compound I[Ce](I)I ZEDZJUDTPVFRNB-UHFFFAOYSA-K 0.000 description 1
- MOOUSOJAOQPDEH-UHFFFAOYSA-K cerium(iii) bromide Chemical compound [Br-].[Br-].[Br-].[Ce+3] MOOUSOJAOQPDEH-UHFFFAOYSA-K 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- GBLDKMKYYYAAKD-UHFFFAOYSA-K dysprosium(3+);tribromide Chemical compound [Br-].[Br-].[Br-].[Dy+3] GBLDKMKYYYAAKD-UHFFFAOYSA-K 0.000 description 1
- XSVCYDUEICANRJ-UHFFFAOYSA-K dysprosium(3+);trifluoromethanesulfonate Chemical compound [Dy+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F XSVCYDUEICANRJ-UHFFFAOYSA-K 0.000 description 1
- 239000012156 elution solvent Substances 0.000 description 1
- GZTUDAKVGXUNIM-UHFFFAOYSA-K erbium(3+);tribromide Chemical compound Br[Er](Br)Br GZTUDAKVGXUNIM-UHFFFAOYSA-K 0.000 description 1
- OKVQKDALNLHZLB-UHFFFAOYSA-K erbium(3+);triiodide Chemical compound I[Er](I)I OKVQKDALNLHZLB-UHFFFAOYSA-K 0.000 description 1
- HDGGAKOVUDZYES-UHFFFAOYSA-K erbium(iii) chloride Chemical compound Cl[Er](Cl)Cl HDGGAKOVUDZYES-UHFFFAOYSA-K 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 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 description 1
- MZNSYJWLQLXLHE-UHFFFAOYSA-K holmium(3+);tribromide Chemical compound Br[Ho](Br)Br MZNSYJWLQLXLHE-UHFFFAOYSA-K 0.000 description 1
- KXCRAPCRWWGWIW-UHFFFAOYSA-K holmium(3+);triiodide Chemical compound I[Ho](I)I KXCRAPCRWWGWIW-UHFFFAOYSA-K 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- 150000004694 iodide salts Chemical class 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229950010610 lutetium chloride Drugs 0.000 description 1
- DWHGOINJUKABSY-UHFFFAOYSA-K lutetium(3+);tribromide Chemical compound [Br-].[Br-].[Br-].[Lu+3] DWHGOINJUKABSY-UHFFFAOYSA-K 0.000 description 1
- NZOCXFRGADJTKP-UHFFFAOYSA-K lutetium(3+);triiodide Chemical compound I[Lu](I)I NZOCXFRGADJTKP-UHFFFAOYSA-K 0.000 description 1
- AEDROEGYZIARPU-UHFFFAOYSA-K lutetium(iii) chloride Chemical compound Cl[Lu](Cl)Cl AEDROEGYZIARPU-UHFFFAOYSA-K 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
- 229910052756 noble gas Inorganic materials 0.000 description 1
- 150000002835 noble gases Chemical class 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- IKUJAIDSWVXUGG-UHFFFAOYSA-N prop-1-enyl acetate Chemical group CC=COC(C)=O IKUJAIDSWVXUGG-UHFFFAOYSA-N 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- HQSWGSFQSCMHFQ-UHFFFAOYSA-K thulium(3+);tribromide Chemical compound [Br-].[Br-].[Br-].[Tm+3] HQSWGSFQSCMHFQ-UHFFFAOYSA-K 0.000 description 1
- LZOMHYVAEHYDST-UHFFFAOYSA-K thulium(3+);triiodide Chemical compound I[Tm](I)I LZOMHYVAEHYDST-UHFFFAOYSA-K 0.000 description 1
- ILOTUXNTERMOJL-UHFFFAOYSA-K thulium(iii) chloride Chemical compound Cl[Tm](Cl)Cl ILOTUXNTERMOJL-UHFFFAOYSA-K 0.000 description 1
- LTSUHJWLSNQKIP-UHFFFAOYSA-J tin(iv) bromide Chemical compound Br[Sn](Br)(Br)Br LTSUHJWLSNQKIP-UHFFFAOYSA-J 0.000 description 1
- YUOWTJMRMWQJDA-UHFFFAOYSA-J tin(iv) fluoride Chemical compound [F-].[F-].[F-].[F-].[Sn+4] YUOWTJMRMWQJDA-UHFFFAOYSA-J 0.000 description 1
- QPBYLOWPSRZOFX-UHFFFAOYSA-J tin(iv) iodide Chemical compound I[Sn](I)(I)I QPBYLOWPSRZOFX-UHFFFAOYSA-J 0.000 description 1
- PYOOBRULIYNHJR-UHFFFAOYSA-K trichloroholmium Chemical compound Cl[Ho](Cl)Cl PYOOBRULIYNHJR-UHFFFAOYSA-K 0.000 description 1
- LEYFXTUKPKKWMP-UHFFFAOYSA-K trichloroytterbium;hexahydrate Chemical compound O.O.O.O.O.O.Cl[Yb](Cl)Cl LEYFXTUKPKKWMP-UHFFFAOYSA-K 0.000 description 1
- FWQVINSGEXZQHB-UHFFFAOYSA-K trifluorodysprosium Chemical compound F[Dy](F)F FWQVINSGEXZQHB-UHFFFAOYSA-K 0.000 description 1
- QGJSAGBHFTXOTM-UHFFFAOYSA-K trifluoroerbium Chemical compound F[Er](F)F QGJSAGBHFTXOTM-UHFFFAOYSA-K 0.000 description 1
- AATUHDXSJTXIHB-UHFFFAOYSA-K trifluorothulium Chemical compound F[Tm](F)F AATUHDXSJTXIHB-UHFFFAOYSA-K 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- LSSJSIMBIIVSTN-UHFFFAOYSA-K ytterbium(3+);triiodide Chemical compound I[Yb](I)I LSSJSIMBIIVSTN-UHFFFAOYSA-K 0.000 description 1
- QNLXXQBCQYDKHD-UHFFFAOYSA-K ytterbium(iii) bromide Chemical compound Br[Yb](Br)Br QNLXXQBCQYDKHD-UHFFFAOYSA-K 0.000 description 1
- XASAPYQVQBKMIN-UHFFFAOYSA-K ytterbium(iii) fluoride Chemical compound F[Yb](F)F XASAPYQVQBKMIN-UHFFFAOYSA-K 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/12—Acetic acid esters
- C07C69/14—Acetic acid esters of monohydroxylic compounds
- C07C69/145—Acetic acid esters of monohydroxylic compounds of unsaturated alcohols
- C07C69/157—Acetic acid esters of monohydroxylic compounds of unsaturated alcohols containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/54—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/28—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
- C07C67/293—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/007—Esters of unsaturated alcohols having the esterified hydroxy group bound to an acyclic carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
- C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D319/18—Ethylenedioxybenzenes, not substituted on the hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2002367031 | 2002-12-18 | ||
| JP2003069733 | 2003-03-14 | ||
| JP2003316336 | 2003-09-09 | ||
| PCT/JP2003/016277 WO2004054997A1 (ja) | 2002-12-18 | 2003-12-18 | １−アセトキシ−３−（置換フェニル）プロペン化合物の製造方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20053261D0 NO20053261D0 (no) | 2005-07-04 |
| NO20053261L NO20053261L (no) | 2005-09-16 |
| NO330857B1 true NO330857B1 (no) | 2011-08-01 |
Family
ID=32600726
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20053261A NO330857B1 (no) | 2002-12-18 | 2005-07-04 | Fremgangsmate for a fremstille 1-acetoksy-3-(substituert fenyl)propen-forbindelse. |
| NO20053741A NO331438B1 (no) | 2002-12-18 | 2005-08-04 | 1-acetoksy-3-(substituerte fenyl)propenforbindelser |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20053741A NO331438B1 (no) | 2002-12-18 | 2005-08-04 | 1-acetoksy-3-(substituerte fenyl)propenforbindelser |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US7173148B2 (de) |
| EP (2) | EP1574509B1 (de) |
| JP (1) | JP4020141B2 (de) |
| KR (2) | KR100785154B1 (de) |
| AT (2) | ATE365704T1 (de) |
| AU (1) | AU2003289432A1 (de) |
| NO (2) | NO330857B1 (de) |
| WO (1) | WO2004054997A1 (de) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7524983B2 (en) * | 2005-05-11 | 2009-04-28 | Firmenich Sa | Catalytic scriabine reaction |
| WO2006120639A2 (en) | 2005-05-11 | 2006-11-16 | Firmenich Sa | Catalytic scriabine reaction |
| JP4910383B2 (ja) * | 2005-10-06 | 2012-04-04 | 宇部興産株式会社 | α−メチル−１，３−ベンゼンジオキソール−５−プロパナールの製造法 |
| JP5228920B2 (ja) * | 2006-11-13 | 2013-07-03 | 宇部興産株式会社 | １−アシルオキシ−３−（３，４−メチレンジオキシフェニル）−１−プロペン化合物の製造方法 |
| CN101605774B (zh) * | 2007-02-15 | 2013-05-29 | 宇部兴产株式会社 | 2-甲基-3-（3,4-亚甲二氧苯基）丙醛及其制造方法 |
| JP5387401B2 (ja) * | 2007-03-07 | 2014-01-15 | 宇部興産株式会社 | ２−メチル−３−（３，４−メチレンジオキシフェニル）プロパナールの品質保持方法、及びその製造方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL230107A (de) * | 1957-08-01 | |||
| JPS55141437A (en) * | 1979-04-20 | 1980-11-05 | Toray Ind Inc | Preparation of alkenylcarboxylate derivative |
| DE3162428D1 (en) | 1980-07-04 | 1984-04-05 | Givaudan & Cie Sa | Process for the preparation of dihydrocinnamaldehyde derivatives |
-
2003
- 2003-12-18 KR KR1020057011106A patent/KR100785154B1/ko not_active Expired - Fee Related
- 2003-12-18 AU AU2003289432A patent/AU2003289432A1/en not_active Abandoned
- 2003-12-18 KR KR1020057013591A patent/KR100724594B1/ko not_active Expired - Fee Related
- 2003-12-18 EP EP03780907A patent/EP1574509B1/de not_active Expired - Lifetime
- 2003-12-18 AT AT05014610T patent/ATE365704T1/de active
- 2003-12-18 US US10/539,785 patent/US7173148B2/en not_active Expired - Fee Related
- 2003-12-18 JP JP2005502498A patent/JP4020141B2/ja not_active Expired - Fee Related
- 2003-12-18 EP EP05014610A patent/EP1609775B1/de not_active Expired - Lifetime
- 2003-12-18 WO PCT/JP2003/016277 patent/WO2004054997A1/ja not_active Ceased
- 2003-12-18 AT AT03780907T patent/ATE364590T1/de active
-
2005
- 2005-06-17 US US11/155,971 patent/US20060004213A1/en not_active Abandoned
- 2005-07-04 NO NO20053261A patent/NO330857B1/no not_active IP Right Cessation
- 2005-08-04 NO NO20053741A patent/NO331438B1/no not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| AU2003289432A1 (en) | 2004-07-09 |
| JP4020141B2 (ja) | 2007-12-12 |
| NO20053261L (no) | 2005-09-16 |
| EP1574509B1 (de) | 2007-06-13 |
| JPWO2004054997A1 (ja) | 2006-04-20 |
| US20060069273A1 (en) | 2006-03-30 |
| US7173148B2 (en) | 2007-02-06 |
| US20060004213A1 (en) | 2006-01-05 |
| WO2004054997A1 (ja) | 2004-07-01 |
| NO331438B1 (no) | 2012-01-02 |
| KR100785154B1 (ko) | 2007-12-11 |
| NO20053261D0 (no) | 2005-07-04 |
| KR20050088255A (ko) | 2005-09-02 |
| KR100724594B1 (ko) | 2007-06-04 |
| HK1088604A1 (en) | 2006-11-10 |
| HK1093496A1 (zh) | 2007-03-02 |
| EP1574509A4 (de) | 2006-06-21 |
| EP1609775B1 (de) | 2007-06-27 |
| NO20053741L (no) | 2004-06-21 |
| EP1609775A3 (de) | 2006-01-18 |
| ATE365704T1 (de) | 2007-07-15 |
| EP1609775A2 (de) | 2005-12-28 |
| EP1574509A1 (de) | 2005-09-14 |
| ATE364590T1 (de) | 2007-07-15 |
| KR20050089830A (ko) | 2005-09-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM1K | Lapsed by not paying the annual fees |