DE69913735T2 - Verfahren zu herstellung von 5-(alfa-hydroxyalkyl)benzo-[1,3]dioxolane - Google Patents
Verfahren zu herstellung von 5-(alfa-hydroxyalkyl)benzo-[1,3]dioxolane Download PDFInfo
- Publication number
- DE69913735T2 DE69913735T2 DE69913735T DE69913735T DE69913735T2 DE 69913735 T2 DE69913735 T2 DE 69913735T2 DE 69913735 T DE69913735 T DE 69913735T DE 69913735 T DE69913735 T DE 69913735T DE 69913735 T2 DE69913735 T2 DE 69913735T2
- Authority
- DE
- Germany
- Prior art keywords
- benzo
- dioxole
- reaction
- formula
- vii
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 title claims abstract description 52
- 238000004519 manufacturing process Methods 0.000 title description 4
- 238000006243 chemical reaction Methods 0.000 claims abstract description 40
- 238000000034 method Methods 0.000 claims abstract description 35
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 18
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 14
- 150000001875 compounds Chemical class 0.000 claims description 19
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 16
- 230000009021 linear effect Effects 0.000 claims description 13
- 239000003054 catalyst Substances 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 11
- ABADUMLIAZCWJD-UHFFFAOYSA-N 1,3-dioxole Chemical compound C1OC=CO1 ABADUMLIAZCWJD-UHFFFAOYSA-N 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 239000011541 reaction mixture Substances 0.000 claims description 9
- -1 aliphatic anhydride Chemical class 0.000 claims description 5
- PXFYAFDHWSXVLU-UHFFFAOYSA-N 1-(3,4-Methylenedioxyphenyl)-propane-1-ol Chemical compound CCC(O)C1=CC=C2OCOC2=C1 PXFYAFDHWSXVLU-UHFFFAOYSA-N 0.000 claims description 4
- MYEIDJPOUKASEC-UHFFFAOYSA-N Dihydrosafrole Chemical compound CCCC1=CC=C2OCOC2=C1 MYEIDJPOUKASEC-UHFFFAOYSA-N 0.000 claims description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- RMNWUXPEDRCTHB-UHFFFAOYSA-N 5-prop-1-enyl-1,3-benzodioxole Chemical group CC=CC1=CC=C2OCOC2=C1.CC=CC1=CC=C2OCOC2=C1 RMNWUXPEDRCTHB-UHFFFAOYSA-N 0.000 claims description 3
- TUCIXUDAQRPDCG-UHFFFAOYSA-N benzene-1,2-diol Chemical compound OC1=CC=CC=C1O.OC1=CC=CC=C1O TUCIXUDAQRPDCG-UHFFFAOYSA-N 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 238000006297 dehydration reaction Methods 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 239000011737 fluorine Chemical group 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 150000002496 iodine Chemical class 0.000 claims description 2
- 239000011630 iodine Chemical group 0.000 claims description 2
- 229920000137 polyphosphoric acid Polymers 0.000 claims description 2
- 230000018044 dehydration Effects 0.000 claims 1
- APUCQYMTNZQNDR-UHFFFAOYSA-N n,n-dimethylazete-2-carboxamide Chemical compound CN(C)C(=O)C1=NC=C1 APUCQYMTNZQNDR-UHFFFAOYSA-N 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 abstract description 16
- 238000005917 acylation reaction Methods 0.000 abstract description 8
- 230000010933 acylation Effects 0.000 abstract description 7
- 239000002917 insecticide Substances 0.000 abstract description 5
- 230000003197 catalytic effect Effects 0.000 abstract description 2
- 230000007613 environmental effect Effects 0.000 abstract description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- 239000000203 mixture Substances 0.000 description 22
- 239000000047 product Substances 0.000 description 19
- 239000003153 chemical reaction reagent Substances 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 150000008064 anhydrides Chemical class 0.000 description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 7
- 238000006722 reduction reaction Methods 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 238000007792 addition Methods 0.000 description 5
- 150000005528 benzodioxoles Chemical class 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 239000002304 perfume Substances 0.000 description 5
- SATCULPHIDQDRE-UHFFFAOYSA-N piperonal Chemical compound O=CC1=CC=C2OCOC2=C1 SATCULPHIDQDRE-UHFFFAOYSA-N 0.000 description 5
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 4
- XILIYVSXLSWUAI-UHFFFAOYSA-N 2-(diethylamino)ethyl n'-phenylcarbamimidothioate;dihydrobromide Chemical compound Br.Br.CCN(CC)CCSC(N)=NC1=CC=CC=C1 XILIYVSXLSWUAI-UHFFFAOYSA-N 0.000 description 4
- RVBJGSPBFIUTTR-UHFFFAOYSA-N 3,4-Methylenedioxypropiophenone Chemical compound CCC(=O)C1=CC=C2OCOC2=C1 RVBJGSPBFIUTTR-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000000010 aprotic solvent Substances 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- NRSXSFHVWXSMOO-UHFFFAOYSA-N 5-prop-2-enyl-3a,4-dihydro-1,3-benzodioxole Chemical compound C1C(CC=C)=CC=C2OCOC21 NRSXSFHVWXSMOO-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- BHUIUXNAPJIDOG-UHFFFAOYSA-N Piperonol Chemical compound OCC1=CC=C2OCOC2=C1 BHUIUXNAPJIDOG-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 150000007529 inorganic bases Chemical class 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- VHVOLFRBFDOUSH-NSCUHMNNSA-N Isosafrole Chemical compound C\C=C\C1=CC=C2OCOC2=C1 VHVOLFRBFDOUSH-NSCUHMNNSA-N 0.000 description 2
- VHVOLFRBFDOUSH-UHFFFAOYSA-N Isosafrole Natural products CC=CC1=CC=C2OCOC2=C1 VHVOLFRBFDOUSH-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000005605 benzo group Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- 239000003205 fragrance Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229940081310 piperonal Drugs 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- 229910052707 ruthenium Inorganic materials 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 238000005809 transesterification reaction Methods 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- 125000006833 (C1-C5) alkylene group Chemical group 0.000 description 1
- ZHKALZZEGVFZQA-UHFFFAOYSA-N 1-(1,3-benzodioxol-5-yl)ethanol Chemical compound CC(O)C1=CC=C2OCOC2=C1 ZHKALZZEGVFZQA-UHFFFAOYSA-N 0.000 description 1
- HBQUIIALDZGRDX-UHFFFAOYSA-N 5-prop-2-enyl-1,3-benzodioxole Chemical compound C=CCC1=CC=C2OCOC2=C1.C=CCC1=CC=C2OCOC2=C1 HBQUIIALDZGRDX-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- CFQSIYDPHWZRTM-UHFFFAOYSA-N F[Br]Cl Chemical compound F[Br]Cl CFQSIYDPHWZRTM-UHFFFAOYSA-N 0.000 description 1
- 238000003747 Grignard reaction Methods 0.000 description 1
- 229910010082 LiAlH Inorganic materials 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 244000227633 Ocotea pretiosa Species 0.000 description 1
- 235000004263 Ocotea pretiosa Nutrition 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 239000002781 deodorant agent Substances 0.000 description 1
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 239000000686 essence Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 229930003944 flavone Natural products 0.000 description 1
- 150000002213 flavones Chemical class 0.000 description 1
- 235000011949 flavones Nutrition 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 208000019423 liver disease Diseases 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 239000005445 natural material Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Substances [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000035943 smell Effects 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000010457 zeolite Substances 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
- C07D317/44—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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Fats And Perfumes (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITMI982857 | 1998-12-30 | ||
| IT1998MI002857A IT1304513B1 (it) | 1998-12-30 | 1998-12-30 | Processo per la sintesi di 5-(alfa-idrossialchil)benzo(1,3)diossoli. |
| PCT/EP1999/007743 WO2000040575A1 (en) | 1998-12-30 | 1999-10-14 | PROCESS FOR THE SYNTHESIS OF 5-(α -HYDROXYALKYL) BENZO[1, 3]DIOXOLS |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69913735D1 DE69913735D1 (de) | 2004-01-29 |
| DE69913735T2 true DE69913735T2 (de) | 2004-07-29 |
Family
ID=11381378
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69913735T Expired - Lifetime DE69913735T2 (de) | 1998-12-30 | 1999-10-14 | Verfahren zu herstellung von 5-(alfa-hydroxyalkyl)benzo-[1,3]dioxolane |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US6342613B1 (enExample) |
| EP (1) | EP1140894B1 (enExample) |
| JP (1) | JP4845266B2 (enExample) |
| KR (1) | KR100682160B1 (enExample) |
| CN (1) | CN1138769C (enExample) |
| AT (1) | ATE256676T1 (enExample) |
| AU (1) | AU756172B2 (enExample) |
| BR (1) | BR9916471B1 (enExample) |
| CA (1) | CA2352249C (enExample) |
| DE (1) | DE69913735T2 (enExample) |
| IT (1) | IT1304513B1 (enExample) |
| RU (1) | RU2243224C2 (enExample) |
| WO (1) | WO2000040575A1 (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4436369B2 (ja) * | 2004-01-28 | 2010-03-24 | エフ．ホフマン−ラ ロシュ アーゲー | スピロ−ベンゾジオキソール類およびそれらのｃｂ１アンタゴニストとしての使用 |
| WO2010079423A1 (en) * | 2009-01-12 | 2010-07-15 | Council Of Scientific & Industrial Research | Inhibitors of phosphatidylinositol-3-kinase (pi3) and inducers of nitric oxide (no) |
| EP2289889A1 (en) | 2009-08-18 | 2011-03-02 | Endura S.p.a. | Substituted alkynyl phenoxy compounds and their uses |
| CN102070596B (zh) * | 2011-01-22 | 2013-02-27 | 浙江大学 | 二氢黄樟素的制备方法 |
| GB201104156D0 (en) | 2011-03-11 | 2011-04-27 | Rothamstead Res Ltd | Compositions and methods for controlling pesticide resistant pests |
| EP3141116B1 (en) | 2015-09-09 | 2018-06-13 | Endura S.p.a. | 5,7-disubstituted 2,3-dihydrobenzofurans and their use as synergists |
| EP3141115A1 (en) | 2015-09-09 | 2017-03-15 | Endura S.p.a. | Substituted methylenedioxybenzyl compounds and their uses as synergists |
| CN106632228B (zh) * | 2016-08-05 | 2019-07-02 | 成都建中香料香精有限公司 | 一种二氢黄樟素的制备方法 |
| WO2018150230A1 (en) | 2017-02-14 | 2018-08-23 | Anthea Aromatics Private Limited | A process for preparation of alkenyl and alkyl derivatives of alkylenedioxybenzene |
| WO2022161628A1 (en) * | 2021-01-29 | 2022-08-04 | Endura S.P.A. | Process for the preparation of 3,4-methylenedioxypropiophenone |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1097270A (en) * | 1965-10-13 | 1968-01-03 | Shell Int Research | Process for the preparation of methylene dioxybenzene, 1,3-benzoxathiole and derivatives thereof |
| US3908000A (en) * | 1971-03-19 | 1975-09-23 | Hoffmann La Roche | Propynyl benzyl ethers as insecticidal agents |
| US3946040A (en) * | 1971-03-19 | 1976-03-23 | Hoffmann-La Roche Inc. | Propynyl benzyl ethers |
| CH583677A5 (enExample) * | 1972-02-03 | 1977-01-14 | Basf Ag | |
| JPS56164178A (en) * | 1980-05-23 | 1981-12-17 | Mitsubishi Chem Ind Ltd | Preparation of 4-hydroxy-1,3-benzodioxole |
| EP0095454A3 (de) * | 1982-05-13 | 1985-04-03 | Gerot-Pharmazeutika Gesellschaft m.b.H. | Neue kernsubstituierte Pyrogallol-Derivate |
| JP2521739B2 (ja) * | 1987-01-27 | 1996-08-07 | 新日本薬品株式会社 | 肝臓疾患治療剤 |
| DE3768658D1 (de) * | 1987-08-03 | 1991-04-18 | Delagrange Lab | 1,4-dihydropyridine, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel. |
| US5420301A (en) * | 1988-03-18 | 1995-05-30 | Ciba-Geigy Corporation | Process for the preparation of substituted difluorobenzo-1,3-dioxoles |
| JP2760998B2 (ja) * | 1988-08-16 | 1998-06-04 | 新日本薬品株式会社 | 肝臓疾患治療剤 |
| SU1703648A1 (ru) * | 1989-12-26 | 1992-01-07 | Туркменский Государственный Университет Им.А.М.Горького | 2-/2-Цианоэтил/-4,5-бензо-1,3-диоксолан, обладающий акарицидной активностью против иксодовых клещей рода Шаломма |
| DE4133155A1 (de) * | 1991-10-07 | 1993-04-08 | Bayer Ag | Verfahren zur herstellung von 2,2-difluorbenzo (1,3)-dioxol-carbaldehyden und neuen zwischenprodukten |
| US5696301A (en) * | 1996-01-23 | 1997-12-09 | Ube Industries, Ltd. | Process for preparing protocatechualdehyde |
-
1998
- 1998-12-30 IT IT1998MI002857A patent/IT1304513B1/it active
-
1999
- 1999-10-14 JP JP2000592283A patent/JP4845266B2/ja not_active Expired - Lifetime
- 1999-10-14 RU RU2001117199/04A patent/RU2243224C2/ru active
- 1999-10-14 US US09/856,752 patent/US6342613B1/en not_active Expired - Lifetime
- 1999-10-14 CN CNB998151173A patent/CN1138769C/zh not_active Expired - Lifetime
- 1999-10-14 CA CA002352249A patent/CA2352249C/en not_active Expired - Lifetime
- 1999-10-14 KR KR1020017007081A patent/KR100682160B1/ko not_active Expired - Lifetime
- 1999-10-14 AU AU10377/00A patent/AU756172B2/en not_active Expired
- 1999-10-14 WO PCT/EP1999/007743 patent/WO2000040575A1/en not_active Ceased
- 1999-10-14 AT AT99953826T patent/ATE256676T1/de not_active IP Right Cessation
- 1999-10-14 BR BRPI9916471-0A patent/BR9916471B1/pt not_active IP Right Cessation
- 1999-10-14 EP EP99953826A patent/EP1140894B1/en not_active Expired - Lifetime
- 1999-10-14 DE DE69913735T patent/DE69913735T2/de not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| ITMI982857A1 (it) | 2000-06-30 |
| ITMI982857A0 (it) | 1998-12-30 |
| BR9916471B1 (pt) | 2010-12-14 |
| EP1140894B1 (en) | 2003-12-17 |
| KR20010083955A (ko) | 2001-09-03 |
| ATE256676T1 (de) | 2004-01-15 |
| CN1332736A (zh) | 2002-01-23 |
| AU1037700A (en) | 2000-07-24 |
| US6342613B1 (en) | 2002-01-29 |
| DE69913735D1 (de) | 2004-01-29 |
| KR100682160B1 (ko) | 2007-02-12 |
| BR9916471A (pt) | 2001-09-18 |
| JP4845266B2 (ja) | 2011-12-28 |
| CA2352249C (en) | 2007-09-11 |
| WO2000040575A1 (en) | 2000-07-13 |
| JP2002534423A (ja) | 2002-10-15 |
| CN1138769C (zh) | 2004-02-18 |
| CA2352249A1 (en) | 2000-07-13 |
| EP1140894A1 (en) | 2001-10-10 |
| RU2243224C2 (ru) | 2004-12-27 |
| AU756172B2 (en) | 2003-01-09 |
| IT1304513B1 (it) | 2001-03-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69913735T2 (de) | Verfahren zu herstellung von 5-(alfa-hydroxyalkyl)benzo-[1,3]dioxolane | |
| DE1468529B2 (de) | Rechtsdrehendes !,S-Dioxo^-ir-carboxyäthyl)-7aß-methyl-5,6,7,7a-tetrahydroindan und Verfahren zu seiner Her- | |
| EP0033928A2 (de) | Verwendung alkylsubstituierter 1,3-Dioxolane als Riechstoffe, sowie diese enthaltende Riechstoffkompositionen | |
| CH672635A5 (enExample) | ||
| DE2159882C3 (de) | Verfahren zur Herstellung niederer Alkylester der cis-Chrysanthemum-monocarbonsäure | |
| DE2729816C2 (de) | 2-Oxy-5-isopropyliden-7-hydroxy-9-substituierte-2,6-methano-3,4,5,6-tetrahydro-2H-1-benzoxocine und Verfahren zu ihrer Herstellung | |
| EP1713755B1 (de) | Verfahren zur herstellung von 2,5-dimethylphenylessigsäure | |
| DE2812288C2 (enExample) | ||
| DE2108649C3 (de) | 2-Methyl-2-hepten-6-on-l-al und seine Acetale | |
| EP0022460B1 (de) | Aliphatische Ether des Hydroximethylcyclododecans und ihre Verwendung zur Herstellung von Riechstoffkompositionen | |
| DE2141309B2 (de) | 5-Cyclohexadecen-l-on-Verfahren zu dessen Herstellung und seine Verwendung als Riechstoff | |
| DE69901196T2 (de) | Verfahren zur Herstellung von CIS-Isoambrettolide und Ihre Anwendung | |
| DE2461605C3 (de) | S-Acetyl-U.e-trimethyltricyclo [53 AO2·7!-dodeca-5-en, Verfahren zu seiner Herstellung und seine Verwendung als Riechstoff | |
| EP0162235B1 (de) | Enantiomerenreine acetalisch mono-geschützte Diole, deren Herstellung und Verwendung | |
| DE1291334B (de) | Verfahren zur Herstellung von 2, 3, 4-Trialkoxy-5-(2'-carboxyaethyl)-7, 8, 9-trihydro-benzocycloheptenen | |
| DE2856721A1 (de) | Verfahren zur herstellung von cyclohex-3-en-1-onen | |
| DE60008697T2 (de) | Verfahren zur Herstellung von 4-(P-methoxyphenyl)-2-amino-butane und Insektizide | |
| DE1468339A1 (de) | Dibenzocycloheptanderivate und Verfahren zu ihrer Herstellung | |
| DE602004010135T2 (de) | Verfahren zur Herstellung von Lactonen und deren Verwendung als Geruchsstoffe | |
| DE19644250A1 (de) | Verfahren zur Herstellung von 2-Methyl-4-(2,2,3-trimethyl-cyclopent-3-en-1-yl)-but-2-en-1-ol | |
| DE2264663C3 (de) | Ungesättigte Sulfoxyde und Verfahren zu ihrer Herstellung | |
| WO2001096277A1 (de) | Verfahren zur herstellung von 2,3,4,6-tetramethylmandelsäure und 2,3,4,6-tetramethylmandelsäureacetat | |
| EP1316554B1 (de) | Acetal-Derivate aus 2-Methyl-2secbutyl-1,3-propandiol und ihre Verwendung als Riechstoff | |
| DE566033C (de) | Verfahren zur Herstellung von Alkyl- bzw. Aryloxyaethylidenestern und Acetalen | |
| DE1217372B (de) | Verfahren zur Herstellung von Cycloalkan- und Cycloalkencarbonsäuren bzw. deren Estern |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition |