HU181328B - Process for producing 7-bracket-e-bracket closed, 9-bracket-z-bracket closed-alkadienol derivatives - Google Patents
Process for producing 7-bracket-e-bracket closed, 9-bracket-z-bracket closed-alkadienol derivatives Download PDFInfo
- Publication number
- HU181328B HU181328B HU811358A HU135881A HU181328B HU 181328 B HU181328 B HU 181328B HU 811358 A HU811358 A HU 811358A HU 135881 A HU135881 A HU 135881A HU 181328 B HU181328 B HU 181328B
- Authority
- HU
- Hungary
- Prior art keywords
- formula
- defined above
- derivative
- solvent
- compound
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 16
- 239000002904 solvent Substances 0.000 claims abstract description 48
- -1 halide ion Chemical class 0.000 claims abstract description 32
- 150000001875 compounds Chemical class 0.000 claims abstract description 30
- 238000002360 preparation method Methods 0.000 claims abstract description 27
- 239000002253 acid Substances 0.000 claims abstract description 15
- 239000011261 inert gas Substances 0.000 claims abstract description 10
- BSAIUMLZVGUGKX-UHFFFAOYSA-N non-2-enal Chemical compound CCCCCCC=CC=O BSAIUMLZVGUGKX-UHFFFAOYSA-N 0.000 claims abstract description 9
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims abstract description 7
- JRZJOMJEPLMPRA-UHFFFAOYSA-N 1-nonene Chemical class CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Substances ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 27
- 239000011541 reaction mixture Substances 0.000 claims description 19
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 14
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 12
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 9
- 239000005977 Ethylene Substances 0.000 claims description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 9
- 206010029897 Obsessive thoughts Diseases 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000000010 aprotic solvent Substances 0.000 claims description 6
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical class CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 230000003197 catalytic effect Effects 0.000 claims description 3
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims 2
- QJKHENCJQIAEBH-UHFFFAOYSA-N (Methylsulfinyl)methanide Chemical compound CS([CH2-])=O QJKHENCJQIAEBH-UHFFFAOYSA-N 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 12
- 241001261104 Lobesia botrana Species 0.000 abstract description 3
- 125000002252 acyl group Chemical group 0.000 abstract description 2
- GYHFUZHODSMOHU-UHFFFAOYSA-N nonanal Chemical class CCCCCCCCC=O GYHFUZHODSMOHU-UHFFFAOYSA-N 0.000 abstract description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 abstract 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 abstract 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 230000002140 halogenating effect Effects 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 230000004936 stimulating effect Effects 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 48
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 47
- 239000000243 solution Substances 0.000 description 45
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 38
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 29
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 26
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 20
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 19
- 235000019341 magnesium sulphate Nutrition 0.000 description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- 239000000203 mixture Substances 0.000 description 16
- 238000005160 1H NMR spectroscopy Methods 0.000 description 14
- 239000011780 sodium chloride Substances 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- ODKORGDBKBYLSR-ZMLDSNJFSA-N [(1Z)-dodeca-1,3-dienyl] acetate Chemical compound C(C)(=O)O\C=C/C=CCCCCCCCC ODKORGDBKBYLSR-ZMLDSNJFSA-N 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 238000004458 analytical method Methods 0.000 description 9
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 8
- 238000004440 column chromatography Methods 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 235000017557 sodium bicarbonate Nutrition 0.000 description 7
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- AEPMMTRERWOSHG-BUAZCGNSSA-N (1Z)-dodeca-1,3-dien-1-ol Chemical compound CCCCCCCCC=C\C=C/O AEPMMTRERWOSHG-BUAZCGNSSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 4
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical class [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000001632 sodium acetate Substances 0.000 description 4
- 235000017281 sodium acetate Nutrition 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- VSOPTMREESZTBI-GQCTYLIASA-N (e)-9-hydroxynon-2-enal Chemical compound OCCCCCC\C=C\C=O VSOPTMREESZTBI-GQCTYLIASA-N 0.000 description 3
- HUHXLHLWASNVDB-UHFFFAOYSA-N 2-(oxan-2-yloxy)oxane Chemical compound O1CCCCC1OC1OCCCC1 HUHXLHLWASNVDB-UHFFFAOYSA-N 0.000 description 3
- VCEVTCDKSHGBSX-UHFFFAOYSA-N 3,3,3-triphenylpropylphosphanium;iodide Chemical compound [I-].C=1C=CC=CC=1C(C=1C=CC=CC=1)(CC[PH3+])C1=CC=CC=C1 VCEVTCDKSHGBSX-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 150000002681 magnesium compounds Chemical class 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- LFGKBRWYZJPYFD-UHFFFAOYSA-N 9,9-dimethoxynon-6-en-1-ol Chemical compound COC(CC=CCCCCCO)OC LFGKBRWYZJPYFD-UHFFFAOYSA-N 0.000 description 2
- WPMBMYHTUSAQIS-UHFFFAOYSA-N 9,9-dimethoxynon-7-enyl acetate Chemical compound COC(OC)C=CCCCCCCOC(C)=O WPMBMYHTUSAQIS-UHFFFAOYSA-N 0.000 description 2
- UVVUXKWPULZIMQ-UHFFFAOYSA-N 9,9-dimethoxynonyl acetate Chemical compound COC(OC)CCCCCCCCOC(C)=O UVVUXKWPULZIMQ-UHFFFAOYSA-N 0.000 description 2
- LIOHXTBHAXATAT-UHFFFAOYSA-N 9-oxononyl acetate Chemical compound CC(=O)OCCCCCCCCC=O LIOHXTBHAXATAT-UHFFFAOYSA-N 0.000 description 2
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 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 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 235000014787 Vitis vinifera Nutrition 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 229960004217 benzyl alcohol Drugs 0.000 description 2
- VHAXQSFPTJUMLT-UHFFFAOYSA-N bis(3-methylbutan-2-yl)boron Chemical compound CC(C)C(C)[B]C(C)C(C)C VHAXQSFPTJUMLT-UHFFFAOYSA-N 0.000 description 2
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 239000002026 chloroform extract Substances 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- HCJWWBBBSCXJMS-UHFFFAOYSA-J copper;dilithium;tetrachloride Chemical compound [Li+].[Li+].[Cl-].[Cl-].[Cl-].[Cl-].[Cu+2] HCJWWBBBSCXJMS-UHFFFAOYSA-J 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- RKQNZHQHJGBYAE-UHFFFAOYSA-N (8-bromo-9,9-dimethoxynonyl) acetate Chemical compound C(C)(=O)OCCCCCCCC(C(OC)OC)Br RKQNZHQHJGBYAE-UHFFFAOYSA-N 0.000 description 1
- VUHHFDCJBPQNDI-VAWYXSNFSA-N (E)-dodec-1-en-9-yn-1-ol Chemical compound C(=C\CCCCCCC#CCC)/O VUHHFDCJBPQNDI-VAWYXSNFSA-N 0.000 description 1
- BSAIUMLZVGUGKX-BQYQJAHWSA-N (E)-non-2-enal Chemical compound CCCCCC\C=C\C=O BSAIUMLZVGUGKX-BQYQJAHWSA-N 0.000 description 1
- CQKHFONAFZDDKV-QXMHVHEDSA-N (Z)-dodec-1-en-1-ol Chemical compound CCCCCCCCCC\C=C/O CQKHFONAFZDDKV-QXMHVHEDSA-N 0.000 description 1
- NDQXKKFRNOPRDW-UHFFFAOYSA-N 1,1,1-triethoxyethane Chemical compound CCOC(C)(OCC)OCC NDQXKKFRNOPRDW-UHFFFAOYSA-N 0.000 description 1
- VEMBMVKAMZZYLP-UHFFFAOYSA-N 1-(2-bromoethoxy)-1-ethoxyethane Chemical compound CCOC(C)OCCBr VEMBMVKAMZZYLP-UHFFFAOYSA-N 0.000 description 1
- SZZINZURZKQZLG-UHFFFAOYSA-N 2-(4-chlorobutoxy)oxane Chemical compound ClCCCCOC1CCCCO1 SZZINZURZKQZLG-UHFFFAOYSA-N 0.000 description 1
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 1
- DCBJCKDOZLTTDW-UHFFFAOYSA-N 5-chloropentan-1-ol Chemical compound OCCCCCCl DCBJCKDOZLTTDW-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- DMJGAUUKIJRBDM-UHFFFAOYSA-N 8-[bis(3-methylbutan-2-yl)boranyl]oct-7-enyl acetate Chemical compound C(C)(=O)OCCCCCCC=CB(C(C)C(C)C)C(C)C(C)C DMJGAUUKIJRBDM-UHFFFAOYSA-N 0.000 description 1
- PTXBQEGVSOMDOW-UHFFFAOYSA-N 8-bromo-9,9-dimethoxynonan-1-ol Chemical compound COC(OC)C(Br)CCCCCCCO PTXBQEGVSOMDOW-UHFFFAOYSA-N 0.000 description 1
- BPNDDHGFNWYFAZ-UHFFFAOYSA-N 9,9-dimethoxynon-7-en-1-ol Chemical compound COC(OC)C=CCCCCCCO BPNDDHGFNWYFAZ-UHFFFAOYSA-N 0.000 description 1
- BCKOXYRJSUXWQH-UHFFFAOYSA-N 9-oxonon-7-enyl acetate Chemical compound CC(=O)OCCCCCCC=CC=O BCKOXYRJSUXWQH-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- VFGZBCKUHOHPKQ-UHFFFAOYSA-N C=C.C(C)(=O)OCCCCCCCCC=O Chemical group C=C.C(C)(=O)OCCCCCCCCC=O VFGZBCKUHOHPKQ-UHFFFAOYSA-N 0.000 description 1
- JTAIPYZSDCLWGS-UHFFFAOYSA-N C=C.OCCCCCCC=CC=O Chemical group C=C.OCCCCCCC=CC=O JTAIPYZSDCLWGS-UHFFFAOYSA-N 0.000 description 1
- 125000006519 CCH3 Chemical group 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- 239000000877 Sex Attractant Substances 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- 241000219095 Vitis Species 0.000 description 1
- 235000009754 Vitis X bourquina Nutrition 0.000 description 1
- 235000012333 Vitis X labruscana Nutrition 0.000 description 1
- 240000006365 Vitis vinifera Species 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- TZAJXUJFGQCTOK-UHFFFAOYSA-N [Li]CCCOCCOCC Chemical compound [Li]CCCOCCOCC TZAJXUJFGQCTOK-UHFFFAOYSA-N 0.000 description 1
- RZBPZGONSGASLN-UHFFFAOYSA-L [Zn+2].[Br-].[Br-].Br Chemical compound [Zn+2].[Br-].[Br-].Br RZBPZGONSGASLN-UHFFFAOYSA-L 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910000085 borane Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 230000007123 defense Effects 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- MQIKJSYMMJWAMP-UHFFFAOYSA-N dicobalt octacarbonyl Chemical group [Co+2].[Co+2].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-] MQIKJSYMMJWAMP-UHFFFAOYSA-N 0.000 description 1
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- HXJFQNUWPUICNY-UHFFFAOYSA-N disiamylborane Chemical compound CC(C)C(C)BC(C)C(C)C HXJFQNUWPUICNY-UHFFFAOYSA-N 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical compound [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 150000004820 halides Chemical group 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 239000002035 hexane extract Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 238000005949 ozonolysis reaction Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 229940125723 sedative agent Drugs 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 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 description 1
- 125000005490 tosylate group Chemical group 0.000 description 1
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C07D317/10—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 not condensed with other rings
- C07D317/14—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 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
- C07D317/20—Free hydroxyl or mercaptan
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/32—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions without formation of -OH groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/30—Compounds having groups
- C07C43/315—Compounds having groups containing oxygen atoms singly bound to carbon atoms not being acetal carbon atoms
-
- 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
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
- C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
- C07C45/59—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/02—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen
- C07C47/19—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen containing hydroxy groups
-
- 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
- C07C67/287—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group by introduction of halogen; by substitution of halogen atoms by other halogen 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
- C07C67/29—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group by introduction of oxygen-containing functional groups
-
- 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
- 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
- C07C67/297—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/62—Halogen-containing esters
- C07C69/63—Halogen-containing esters of saturated acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (10)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
HU811358A HU181328B (en) | 1981-05-15 | 1981-05-15 | Process for producing 7-bracket-e-bracket closed, 9-bracket-z-bracket closed-alkadienol derivatives |
BE1/10513A BE893152A (fr) | 1981-05-15 | 1982-05-12 | Procede de preparation de derives de (7e-9z)-alcadienols |
YU01017/82A YU101782A (en) | 1981-05-15 | 1982-05-13 | Process for obtaining (7e,9z)-alkadienol derivatives |
FR8208332A FR2505820B1 (fr) | 1981-05-15 | 1982-05-13 | Procede de preparation de derives de (7e-9z)-alcadienols |
GB8213990A GB2098609B (en) | 1981-05-15 | 1982-05-13 | Process for the preparation of /7e,9z/-alkadienol derivatives |
CS823484A CS226740B2 (en) | 1981-05-15 | 1982-05-13 | Method of preparing (7e,9z)-alkadienol derivatives |
GR68156A GR76012B (it) | 1981-05-15 | 1982-05-14 | |
IT21254/82A IT1190823B (it) | 1981-05-15 | 1982-05-14 | Procedimento per la preparazione di derivati del (7e,9z)-alcadienolo |
SU823441301A SU1356957A3 (ru) | 1981-05-15 | 1982-05-14 | Способ получени ацетата 7(Е)-9(Z)додекадиенола |
ES512230A ES512230A0 (es) | 1981-05-15 | 1982-05-14 | "procedimiento de preparacion de derivados (7e,9z)-alcadienoles". |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
HU811358A HU181328B (en) | 1981-05-15 | 1981-05-15 | Process for producing 7-bracket-e-bracket closed, 9-bracket-z-bracket closed-alkadienol derivatives |
Publications (1)
Publication Number | Publication Date |
---|---|
HU181328B true HU181328B (en) | 1983-07-28 |
Family
ID=10954100
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HU811358A HU181328B (en) | 1981-05-15 | 1981-05-15 | Process for producing 7-bracket-e-bracket closed, 9-bracket-z-bracket closed-alkadienol derivatives |
Country Status (10)
Country | Link |
---|---|
BE (1) | BE893152A (it) |
CS (1) | CS226740B2 (it) |
ES (1) | ES512230A0 (it) |
FR (1) | FR2505820B1 (it) |
GB (1) | GB2098609B (it) |
GR (1) | GR76012B (it) |
HU (1) | HU181328B (it) |
IT (1) | IT1190823B (it) |
SU (1) | SU1356957A3 (it) |
YU (1) | YU101782A (it) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3721536A1 (de) * | 1986-07-18 | 1988-01-21 | Basf Ag | Verfahren und mittel zur bekaempfung des bekreuzten traubenwicklers |
DE3726511A1 (de) * | 1987-08-08 | 1989-02-16 | Basf Ag | 1,1-dialkoxy- oder 1,1-((alpha),(omega)-methylendioxy)-non-2-in-9-ol und deren oh-geschuetzte derivate |
DE3729225A1 (de) * | 1987-09-02 | 1989-03-23 | Basf Ag | 9-hydroxydodec-10-enyl-1-t-butylether und seine verwendung als zwischenprodukt zur synthese von 8,10-dodecadienol |
DE3815044A1 (de) * | 1988-05-04 | 1989-11-16 | Basf Ag | 1-tert.-butoxy-(omega)-alkene und deren verwendung als riechstoffe |
DE3815043A1 (de) * | 1988-05-04 | 1989-11-16 | Basf Ag | 3,9-dihydroxynonin und dessen an der 9-oh-funktion geschuetzte derivate |
DE3817399A1 (de) * | 1988-05-21 | 1989-11-30 | Basf Ag | Verfahren zur herstellung von e7/z9-alkadien-1-olen und deren an der hydroxylgruppe geschuetzten derivaten |
US6838576B1 (en) * | 2003-10-23 | 2005-01-04 | 3M Innovative Properties Company | Process for preparing functional group-containing olefinic compounds |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3845108A (en) * | 1973-08-31 | 1974-10-29 | W Roelofs | Trans-7-cis-9-dodecadien-1-yl acetate |
FR2267705A1 (en) * | 1974-04-19 | 1975-11-14 | Anvar | 1-Acetoxy-7,9-dodecadiene - sexual attraction for insect pests |
US3954818A (en) * | 1974-11-25 | 1976-05-04 | Zoecon Corporation | Synthesis of non-4-en-6-ynoic acid ester |
FR2341546A1 (fr) * | 1976-02-20 | 1977-09-16 | Anvar | Nouveau procede de synthese stereoselective de composes dieniques e, z possedant une chaine de 12 a 16 atomes de carbone ainsi que de leurs precurseurs immediats les enynes conjugues e |
-
1981
- 1981-05-15 HU HU811358A patent/HU181328B/hu not_active IP Right Cessation
-
1982
- 1982-05-12 BE BE1/10513A patent/BE893152A/fr not_active IP Right Cessation
- 1982-05-13 FR FR8208332A patent/FR2505820B1/fr not_active Expired
- 1982-05-13 GB GB8213990A patent/GB2098609B/en not_active Expired
- 1982-05-13 CS CS823484A patent/CS226740B2/cs unknown
- 1982-05-13 YU YU01017/82A patent/YU101782A/xx unknown
- 1982-05-14 ES ES512230A patent/ES512230A0/es active Granted
- 1982-05-14 SU SU823441301A patent/SU1356957A3/ru active
- 1982-05-14 GR GR68156A patent/GR76012B/el unknown
- 1982-05-14 IT IT21254/82A patent/IT1190823B/it active
Also Published As
Publication number | Publication date |
---|---|
GB2098609B (en) | 1985-08-14 |
CS226740B2 (en) | 1984-04-16 |
ES8402807A1 (es) | 1984-03-01 |
GR76012B (it) | 1984-08-03 |
SU1356957A3 (ru) | 1987-11-30 |
IT8221254A0 (it) | 1982-05-14 |
FR2505820B1 (fr) | 1985-11-15 |
BE893152A (fr) | 1982-11-12 |
IT1190823B (it) | 1988-02-24 |
ES512230A0 (es) | 1984-03-01 |
GB2098609A (en) | 1982-11-24 |
FR2505820A1 (fr) | 1982-11-19 |
YU101782A (en) | 1985-06-30 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP2019189529A (ja) | 1−ハロアルカジエン及びその製造方法並びに(9e,11z)−9,11−ヘキサデカジエニル=アセテートの製造方法 | |
HU181328B (en) | Process for producing 7-bracket-e-bracket closed, 9-bracket-z-bracket closed-alkadienol derivatives | |
Muchowski et al. | Cyclic phosphonium ylides. A short synthesis of gossyplure | |
JP2690356B2 (ja) | E7/z9―アルカジエン―1―オール及びそのヒドロキシル基で保護された誘導体の製法 | |
HU204044B (en) | Process for producing trans-aryltetraloncarboxylic acid derivatives | |
EP0295880A1 (en) | Substituted cyclic ketones, substituted cyclic enones, and process for producing the same | |
US4851588A (en) | Novel process for the preparation of bronopol | |
US4007217A (en) | Process for producing 2-hydroxy-3-butenoic acid derivatives | |
EP0321432A1 (en) | Process for the preparation of certain substituted aromatic compounds | |
US4083855A (en) | Method for producing a γ-lactone | |
JP3241760B2 (ja) | シクロヘキサノン誘導体 | |
US4395561A (en) | Synthesis of 3-hydroxyoxetane | |
US4258205A (en) | 2,2-Dimethylcyclopropanecarbaldehyde dimethyl acetal derivatives | |
JP2000143688A (ja) | ゼアキサンチンモノ−β−グルコシドの製造方法 | |
GB2111501A (en) | Process for the preparation of 7-methyl-3-methylene-7-octen-1-yl propanoate | |
JPH0245614B2 (it) | ||
BE1001613A4 (fr) | Procede pour la preparation du (+)-13-norfaranal. | |
EP0647624A1 (fr) | Nouveaux intermédiaires de préparation de la vitamine A et des caroténoides et leur procédé de préparation | |
EP0065354B1 (en) | Process for the preparation of 1,1-bis phenyl-2-haloalkan-1-ols | |
JPH07188090A (ja) | ビタミンaおよびカロテノイド類の製造のための新規な中間体並びにそれらの製造方法 | |
CS231994B2 (en) | Manufacturing process of 2-cyclopenane derivatives | |
JP4800933B2 (ja) | シクロプロパンモノアセタール誘導体の製造方法およびその中間体 | |
JP3128703B2 (ja) | 発色性化合物の製造方法及びその中間体類並びにそれらの製造方法 | |
US4071542A (en) | Synthesis of hydroxycyclopenten-1-ones | |
JPH072666B2 (ja) | 3―(3―ハロゲノ―4―アルコキシフェニル)―3―メチルブタナール類の製造方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
HU90 | Patent valid on 900628 | ||
HMM4 | Cancellation of final prot. due to non-payment of fee |