CH643227A5 - Verfahren zur herstellung von cyclohex-3-en-1-on-verbindungen. - Google Patents
Verfahren zur herstellung von cyclohex-3-en-1-on-verbindungen. Download PDFInfo
- Publication number
- CH643227A5 CH643227A5 CH1291878A CH1291878A CH643227A5 CH 643227 A5 CH643227 A5 CH 643227A5 CH 1291878 A CH1291878 A CH 1291878A CH 1291878 A CH1291878 A CH 1291878A CH 643227 A5 CH643227 A5 CH 643227A5
- Authority
- CH
- Switzerland
- Prior art keywords
- reaction mixture
- lewis acid
- solvent
- cyclohex
- compound
- Prior art date
Links
- VNLZLLDMKRKVEX-UHFFFAOYSA-N cyclohex-3-enone Chemical class O=C1CCC=CC1 VNLZLLDMKRKVEX-UHFFFAOYSA-N 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title 1
- 239000011541 reaction mixture Substances 0.000 claims description 61
- 238000000034 method Methods 0.000 claims description 53
- VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 claims description 48
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 43
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 38
- 239000002841 Lewis acid Substances 0.000 claims description 30
- 150000001875 compounds Chemical class 0.000 claims description 29
- 150000007517 lewis acids Chemical class 0.000 claims description 28
- BKPZKBPYOGMMAL-UHFFFAOYSA-N 2-methyl-4-propan-2-ylcyclohex-3-en-1-one Chemical compound CC(C)C1=CC(C)C(=O)CC1 BKPZKBPYOGMMAL-UHFFFAOYSA-N 0.000 claims description 27
- GGOZBGQCWVKOSB-UHFFFAOYSA-N 2-careneepoxide Chemical compound C1CC2(C)OC2C2C(C)(C)C21 GGOZBGQCWVKOSB-UHFFFAOYSA-N 0.000 claims description 25
- 238000006243 chemical reaction Methods 0.000 claims description 22
- 239000002904 solvent Substances 0.000 claims description 21
- BQOFWKZOCNGFEC-UHFFFAOYSA-N carene Chemical compound C1C(C)=CCC2C(C)(C)C12 BQOFWKZOCNGFEC-UHFFFAOYSA-N 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- 229940102001 zinc bromide Drugs 0.000 claims description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 16
- 239000000243 solution Substances 0.000 claims description 16
- -1 cyclohex-3-en-I-one compound Chemical class 0.000 claims description 15
- 239000004593 Epoxy Substances 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 12
- 230000008569 process Effects 0.000 claims description 12
- 238000010992 reflux Methods 0.000 claims description 12
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 claims description 11
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 claims description 10
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 10
- 229930006737 car-3-ene Natural products 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 239000003960 organic solvent Substances 0.000 claims description 7
- 238000003822 preparative gas chromatography Methods 0.000 claims description 7
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 6
- 239000012442 inert solvent Substances 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 229910015900 BF3 Inorganic materials 0.000 claims description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 5
- 238000006735 epoxidation reaction Methods 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 239000007858 starting material Substances 0.000 claims description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 4
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 claims description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 238000000926 separation method Methods 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims 5
- 238000002156 mixing Methods 0.000 claims 4
- 239000007864 aqueous solution Substances 0.000 claims 3
- 238000005194 fractionation Methods 0.000 claims 3
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims 2
- 238000004140 cleaning Methods 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 239000011780 sodium chloride Substances 0.000 claims 1
- 230000001960 triggered effect Effects 0.000 claims 1
- 235000005074 zinc chloride Nutrition 0.000 claims 1
- 239000011592 zinc chloride Substances 0.000 claims 1
- 239000000047 product Substances 0.000 description 21
- 230000008707 rearrangement Effects 0.000 description 13
- 238000005481 NMR spectroscopy Methods 0.000 description 11
- 230000005012 migration Effects 0.000 description 7
- 238000013508 migration Methods 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 6
- 150000002576 ketones Chemical class 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical class CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 4
- 239000003205 fragrance Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohex-2-enone Chemical class O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 238000007157 ring contraction reaction Methods 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 235000007586 terpenes Nutrition 0.000 description 3
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 2
- AGHSZSJVJPSERC-UHFFFAOYSA-N 3,8,8-trimethyl-4-oxatricyclo[5.1.0.03,5]octane Chemical compound C1C2OC2(C)CC2C(C)(C)C21 AGHSZSJVJPSERC-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- MOYAFQVGZZPNRA-UHFFFAOYSA-N Terpinolene Chemical compound CC(C)=C1CCC(C)=CC1 MOYAFQVGZZPNRA-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- WPGPCDVQHXOMQP-UHFFFAOYSA-N carvotanacetone Natural products CC(C)C1CC=C(C)C(=O)C1 WPGPCDVQHXOMQP-UHFFFAOYSA-N 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- PQANGXXSEABURG-UHFFFAOYSA-N cyclohex-2-en-1-ol Chemical compound OC1CCCC=C1 PQANGXXSEABURG-UHFFFAOYSA-N 0.000 description 2
- AZOCECCLWFDTAP-UHFFFAOYSA-N dihydrocarvone Chemical compound CC1CCC(C(C)=C)CC1=O AZOCECCLWFDTAP-UHFFFAOYSA-N 0.000 description 2
- 150000002118 epoxides Chemical class 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 2
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 description 2
- XNMPFDIYAMOYRM-UHFFFAOYSA-N p-mentha-1,3,8-triene Chemical compound CC(=C)C1=CC=C(C)CC1 XNMPFDIYAMOYRM-UHFFFAOYSA-N 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 150000004965 peroxy acids Chemical class 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000011973 solid acid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 150000003505 terpenes Chemical class 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- 239000003039 volatile agent Substances 0.000 description 2
- LFJQCDVYDGGFCH-UHFFFAOYSA-N β-phellandrene Chemical compound CC(C)C1CCC(=C)C=C1 LFJQCDVYDGGFCH-UHFFFAOYSA-N 0.000 description 2
- LGNSZMLHOYDATP-UHFFFAOYSA-N (+)-4-Carene Chemical compound C1=CC(C)CC2C(C)(C)C12 LGNSZMLHOYDATP-UHFFFAOYSA-N 0.000 description 1
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 1
- CCEFMUBVSUDRLG-BBBLOLIVSA-N (+)-trans-limonene oxide Chemical compound C1[C@H](C(=C)C)CC[C@]2(C)O[C@@H]21 CCEFMUBVSUDRLG-BBBLOLIVSA-N 0.000 description 1
- CCEFMUBVSUDRLG-KXUCPTDWSA-N (4R)-limonene 1,2-epoxide Natural products C1[C@H](C(=C)C)CC[C@@]2(C)O[C@H]21 CCEFMUBVSUDRLG-KXUCPTDWSA-N 0.000 description 1
- WEEGYLXZBRQIMU-UHFFFAOYSA-N 1,8-cineole Natural products C1CC2CCC1(C)OC2(C)C WEEGYLXZBRQIMU-UHFFFAOYSA-N 0.000 description 1
- MKPMHJQMNACGDI-UHFFFAOYSA-N 1-methyl-4-prop-1-en-2-ylcyclohex-2-en-1-ol Chemical compound CC(=C)C1CCC(C)(O)C=C1 MKPMHJQMNACGDI-UHFFFAOYSA-N 0.000 description 1
- SCBBUPSCKNUDCO-UHFFFAOYSA-N 1-methyl-4-prop-1-en-2-ylcyclohexa-1,4-diene Chemical compound CC(=C)C1=CCC(C)=CC1 SCBBUPSCKNUDCO-UHFFFAOYSA-N 0.000 description 1
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 1
- GLVYLTSKTCWWJR-UHFFFAOYSA-N 2-carbonoperoxoylbenzoic acid Chemical compound OOC(=O)C1=CC=CC=C1C(O)=O GLVYLTSKTCWWJR-UHFFFAOYSA-N 0.000 description 1
- BPIZZOZTEBWEPT-UHFFFAOYSA-N 2-methyl-4-propan-2-ylcyclohex-2-en-1-one Chemical compound CC(C)C1CCC(=O)C(C)=C1 BPIZZOZTEBWEPT-UHFFFAOYSA-N 0.000 description 1
- ABSCYWMYRVUUIC-UHFFFAOYSA-N 3,7,7-trimethylbicyclo[4.1.0]heptan-4-one Chemical compound C1C(=O)C(C)CC2C(C)(C)C12 ABSCYWMYRVUUIC-UHFFFAOYSA-N 0.000 description 1
- ISFMXVMWEWLJGJ-PAPYEOQZSA-N 4-Epicurcumenol Natural products CC1=C[C@](O2)(O)C(=C(C)C)C[C@@]22[C@H](C)CC[C@H]21 ISFMXVMWEWLJGJ-PAPYEOQZSA-N 0.000 description 1
- RLYSXAZAJUMULG-UHFFFAOYSA-N 6-methyl-3-propan-2-ylcyclohex-2-en-1-one Chemical compound CC(C)C1=CC(=O)C(C)CC1 RLYSXAZAJUMULG-UHFFFAOYSA-N 0.000 description 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
- 244000045410 Aegopodium podagraria Species 0.000 description 1
- 125000006519 CCH3 Chemical group 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000272194 Ciconiiformes Species 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 235000016623 Fragaria vesca Nutrition 0.000 description 1
- 240000009088 Fragaria x ananassa Species 0.000 description 1
- 235000011363 Fragaria x ananassa Nutrition 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CCEFMUBVSUDRLG-XNWIYYODSA-N Limonene-1,2-epoxide Chemical compound C1[C@H](C(=C)C)CCC2(C)OC21 CCEFMUBVSUDRLG-XNWIYYODSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 229920004894 Triton X-305 Polymers 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000004808 allyl alcohols Chemical class 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 125000003583 car-3-ene group Chemical group 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 150000001793 charged compounds Chemical class 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- AZOCECCLWFDTAP-RKDXNWHRSA-N dihydrocarvone Natural products C[C@@H]1CC[C@@H](C(C)=C)CC1=O AZOCECCLWFDTAP-RKDXNWHRSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 229940041616 menthol Drugs 0.000 description 1
- 238000004452 microanalysis Methods 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 229930003658 monoterpene Natural products 0.000 description 1
- 150000002773 monoterpene derivatives Chemical class 0.000 description 1
- 235000002577 monoterpenes Nutrition 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- YHQGMYUVUMAZJR-UHFFFAOYSA-N α-terpinene Chemical compound CC(C)C1=CC=C(C)CC1 YHQGMYUVUMAZJR-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen 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
- C07C45/56—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
- C07C45/58—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 three-membered rings
-
- 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/865,829 US4136119A (en) | 1977-12-30 | 1977-12-30 | M-menthenone and process for its production |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH643227A5 true CH643227A5 (de) | 1984-05-30 |
Family
ID=25346330
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1291878A CH643227A5 (de) | 1977-12-30 | 1978-12-20 | Verfahren zur herstellung von cyclohex-3-en-1-on-verbindungen. |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4136119A (cg-RX-API-DMAC7.html) |
| JP (1) | JPS5498743A (cg-RX-API-DMAC7.html) |
| CH (1) | CH643227A5 (cg-RX-API-DMAC7.html) |
| DE (1) | DE2856721C2 (cg-RX-API-DMAC7.html) |
| ES (1) | ES476452A1 (cg-RX-API-DMAC7.html) |
| FR (1) | FR2413351A1 (cg-RX-API-DMAC7.html) |
| GB (1) | GB2011413B (cg-RX-API-DMAC7.html) |
| NL (1) | NL7812345A (cg-RX-API-DMAC7.html) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4582556A (en) * | 1982-11-22 | 1986-04-15 | Olin Corporation | Adhesion primers for encapsulating epoxies |
| US4808409A (en) * | 1984-08-16 | 1989-02-28 | Board Of Trustees, University Of Illinois | Low cariogenic sweetening agents |
| TW297811B (cg-RX-API-DMAC7.html) * | 1994-09-12 | 1997-02-11 | Sumitomo Chemical Co | |
| JP4029088B2 (ja) * | 2002-05-29 | 2008-01-09 | フイルメニツヒ ソシエテ アノニム | 香料成分としてのヒンダードケトン |
| EP2687586B1 (de) * | 2012-07-17 | 2016-11-23 | Symrise AG | Verwendung definierter Cyclohexenone als Mittel zum überadditiven Verstärken eines Geruchseindrucks sowie Riech- und/oder Geschmacksstoffkomposition |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3009959A (en) * | 1961-11-21 | Figure i | ||
| US1477691A (en) * | 1923-01-02 | 1923-12-18 | Farbenfab Vorm Bayer F & Co | Pharmaceutical product |
| US2790708A (en) * | 1949-06-25 | 1957-04-30 | Blaw Knox Co | System for solvent extraction of oil or the like from solid organic particles |
| US2619504A (en) * | 1950-09-15 | 1952-11-25 | Newport Ind Inc | Process of making 4(5)-p-menthen-3-one |
| US2887479A (en) * | 1955-11-15 | 1959-05-19 | Eastman Kodak Co | Heterocyclic quaternary salts containing a cyclohexenylidenemethyl substituent |
| US2918495A (en) * | 1957-09-30 | 1959-12-22 | Glidden Co | Process for preparing a menthadiene ketone and composition |
| US3151167A (en) * | 1961-04-12 | 1964-09-29 | Diamond Alkali Co | Preparation of ketones from epoxides |
| US3397120A (en) * | 1967-01-13 | 1968-08-13 | Exxon Research Engineering Co | Purification of dihydroisophorone by plural distillation and isomerization |
| US3560571A (en) * | 1967-05-29 | 1971-02-02 | Procter & Gamble | Novel photochemical reaction of 4-caranone and novel reaction products resulting therefrom |
| US3928456A (en) * | 1967-11-09 | 1975-12-23 | Firmenich & Cie | Cycloaliphatic unsaturated ketones as odour- and taste-modifying agents |
| US3538164A (en) * | 1968-02-08 | 1970-11-03 | Reynolds Tobacco Co R | Synthesis of dihydrocarvone |
| US3531528A (en) * | 1968-05-24 | 1970-09-29 | Upjohn Co | 5,6 - diphenyl - 4a - lower - alkyl - 4,4a,7,8-tetrahydro - 2(3h) - naphthalenones and process |
| US3814733A (en) * | 1970-07-27 | 1974-06-04 | Smc Corp | Isomerization of(+)-trans-2,3-epoxy-ciscarane to(+)-cis-2,8-p-methadiene-1-ol |
| US3734930A (en) * | 1971-09-22 | 1973-05-22 | R Razdan | Direct synthesis of ({31 )-trans-{66 {11 tetrahydrocannabinol from olivetol and ({30 )-trans-{66 {11 -carene oxide |
| US3927107A (en) * | 1972-10-26 | 1975-12-16 | Firmenich & Cie | 2,6,6-Trimethyl-1-alkenoyl-cyclohexenones |
-
1977
- 1977-12-30 US US05/865,829 patent/US4136119A/en not_active Expired - Lifetime
-
1978
- 1978-12-20 CH CH1291878A patent/CH643227A5/de not_active IP Right Cessation
- 1978-12-20 NL NL7812345A patent/NL7812345A/xx not_active Application Discontinuation
- 1978-12-25 JP JP15875978A patent/JPS5498743A/ja active Granted
- 1978-12-28 ES ES476452A patent/ES476452A1/es not_active Expired
- 1978-12-29 FR FR7836885A patent/FR2413351A1/fr active Granted
- 1978-12-29 DE DE2856721A patent/DE2856721C2/de not_active Expired
- 1978-12-29 GB GB7850268A patent/GB2011413B/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6223735B2 (cg-RX-API-DMAC7.html) | 1987-05-25 |
| GB2011413B (en) | 1982-06-30 |
| DE2856721A1 (de) | 1979-07-12 |
| FR2413351A1 (fr) | 1979-07-27 |
| NL7812345A (nl) | 1979-07-03 |
| ES476452A1 (es) | 1980-05-16 |
| US4136119A (en) | 1979-01-23 |
| JPS5498743A (en) | 1979-08-03 |
| DE2856721C2 (de) | 1983-11-10 |
| FR2413351B1 (cg-RX-API-DMAC7.html) | 1981-08-14 |
| GB2011413A (en) | 1979-07-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |