DE1923223A1 - Derivate des 1-AEthyl-3,3-dimethyl-cyclo-hexans und Verfahren zu deren Herstellung - Google Patents
Derivate des 1-AEthyl-3,3-dimethyl-cyclo-hexans und Verfahren zu deren HerstellungInfo
- Publication number
- DE1923223A1 DE1923223A1 DE19691923223 DE1923223A DE1923223A1 DE 1923223 A1 DE1923223 A1 DE 1923223A1 DE 19691923223 DE19691923223 DE 19691923223 DE 1923223 A DE1923223 A DE 1923223A DE 1923223 A1 DE1923223 A1 DE 1923223A1
- Authority
- DE
- Germany
- Prior art keywords
- hydrogen
- compound
- formula
- dimethyl
- radical
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 21
- 238000002360 preparation method Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 32
- 239000001257 hydrogen Substances 0.000 claims description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims description 30
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 29
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 23
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
- 239000003205 fragrance Substances 0.000 claims description 14
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 12
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 12
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 12
- 239000003054 catalyst Substances 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 239000002841 Lewis acid Substances 0.000 claims description 9
- 150000007517 lewis acids Chemical class 0.000 claims description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 125000002339 acetoacetyl group Chemical group O=C([*])C([H])([H])C(=O)C([H])([H])[H] 0.000 claims description 7
- 150000002431 hydrogen Chemical group 0.000 claims description 6
- 235000019260 propionic acid Nutrition 0.000 claims description 6
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- HITROERJXNWVOI-SOFGYWHQSA-N (5e)-octa-1,5-diene Chemical compound CC\C=C\CCC=C HITROERJXNWVOI-SOFGYWHQSA-N 0.000 claims description 4
- FUDNBFMOXDUIIE-UHFFFAOYSA-N 3,7-dimethylocta-1,6-diene Chemical compound C=CC(C)CCC=C(C)C FUDNBFMOXDUIIE-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 claims description 4
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000002304 perfume Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 6
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 6
- -1 cyclic alkenes Chemical class 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 5
- 150000007524 organic acids Chemical class 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 229910015900 BF3 Inorganic materials 0.000 description 4
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 4
- 241000220317 Rosa Species 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 4
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 description 4
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 4
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 239000005792 Geraniol Substances 0.000 description 3
- GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 description 3
- 239000001926 citrus aurantium l. subsp. bergamia wright et arn. oil Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 229940093858 ethyl acetoacetate Drugs 0.000 description 3
- 229940113087 geraniol Drugs 0.000 description 3
- WPFVBOQKRVRMJB-UHFFFAOYSA-N hydroxycitronellal Chemical compound O=CCC(C)CCCC(C)(C)O WPFVBOQKRVRMJB-UHFFFAOYSA-N 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 229940067107 phenylethyl alcohol Drugs 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 3
- 239000011592 zinc chloride Substances 0.000 description 3
- 235000005074 zinc chloride Nutrition 0.000 description 3
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 description 2
- QMVPMAAFGQKVCJ-SNVBAGLBSA-N (R)-(+)-citronellol Natural products OCC[C@H](C)CCC=C(C)C QMVPMAAFGQKVCJ-SNVBAGLBSA-N 0.000 description 2
- CDOSHBSSFJOMGT-JTQLQIEISA-N (R)-linalool Natural products CC(C)=CCC[C@@](C)(O)C=C CDOSHBSSFJOMGT-JTQLQIEISA-N 0.000 description 2
- BVUYQSFBRKUJNK-UHFFFAOYSA-N 1-(3,3-dimethylcyclohexyl)ethanol Chemical compound CC(O)C1CCCC(C)(C)C1 BVUYQSFBRKUJNK-UHFFFAOYSA-N 0.000 description 2
- 241000207199 Citrus Species 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 229940007550 benzyl acetate Drugs 0.000 description 2
- JGQFVRIQXUFPAH-UHFFFAOYSA-N beta-citronellol Natural products OCCC(C)CCCC(C)=C JGQFVRIQXUFPAH-UHFFFAOYSA-N 0.000 description 2
- 235000000484 citronellol Nutrition 0.000 description 2
- 235000020971 citrus fruits Nutrition 0.000 description 2
- 235000001671 coumarin Nutrition 0.000 description 2
- 229960000956 coumarin Drugs 0.000 description 2
- PRULABYGUVKYSZ-UHFFFAOYSA-N deca-1,6-diene Chemical compound CCCC=CCCCC=C PRULABYGUVKYSZ-UHFFFAOYSA-N 0.000 description 2
- HFJRKMMYBMWEAD-UHFFFAOYSA-N dodecanal Chemical compound CCCCCCCCCCCC=O HFJRKMMYBMWEAD-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 229930007744 linalool Natural products 0.000 description 2
- UWKAYLJWKGQEPM-LBPRGKRZSA-N linalyl acetate Chemical compound CC(C)=CCC[C@](C)(C=C)OC(C)=O UWKAYLJWKGQEPM-LBPRGKRZSA-N 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 2
- DTUQWGWMVIHBKE-UHFFFAOYSA-N phenylacetaldehyde Chemical compound O=CCC1=CC=CC=C1 DTUQWGWMVIHBKE-UHFFFAOYSA-N 0.000 description 2
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- PSQYTAPXSHCGMF-BQYQJAHWSA-N β-ionone Chemical compound CC(=O)\C=C\C1=C(C)CCCC1(C)C PSQYTAPXSHCGMF-BQYQJAHWSA-N 0.000 description 2
- SFEOKXHPFMOVRM-UHFFFAOYSA-N (+)-(S)-gamma-ionone Natural products CC(=O)C=CC1C(=C)CCCC1(C)C SFEOKXHPFMOVRM-UHFFFAOYSA-N 0.000 description 1
- DXIWBWIDAYBUDF-UHFFFAOYSA-N 1-(3,3-dimethylcyclohexyl)ethanone Chemical compound CC(=O)C1CCCC(C)(C)C1 DXIWBWIDAYBUDF-UHFFFAOYSA-N 0.000 description 1
- BYAGTDRBAUXTFK-UHFFFAOYSA-N 1-(3,5-dimethylcyclohexyl)ethanone Chemical group CC1CC(C)CC(C(C)=O)C1 BYAGTDRBAUXTFK-UHFFFAOYSA-N 0.000 description 1
- OFHHDSQXFXLTKC-UHFFFAOYSA-N 10-undecenal Chemical compound C=CCCCCCCCCC=O OFHHDSQXFXLTKC-UHFFFAOYSA-N 0.000 description 1
- GPQOPWVKNFRPTL-UHFFFAOYSA-N 3-ethyl-1,1-dimethylcyclohexane Chemical class CCC1CCCC(C)(C)C1 GPQOPWVKNFRPTL-UHFFFAOYSA-N 0.000 description 1
- USMNOWBWPHYOEA-UHFFFAOYSA-N 3‐isothujone Chemical compound CC1C(=O)CC2(C(C)C)C1C2 USMNOWBWPHYOEA-UHFFFAOYSA-N 0.000 description 1
- INIOTLARNNSXAE-UHFFFAOYSA-N 4,8-dimethyl-2-propan-2-ylidene-3,3a,4,5,6,8a-hexahydro-1h-azulen-6-ol Chemical compound CC1CC(O)C=C(C)C2CC(=C(C)C)CC12 INIOTLARNNSXAE-UHFFFAOYSA-N 0.000 description 1
- PCFHYANYPQEMPU-UHFFFAOYSA-N 4-(2,2,3-trimethyl-5-bicyclo[2.2.1]heptanyl)cyclohexan-1-ol Chemical compound CC1(C)C(C)C2CC1CC2C1CCC(O)CC1 PCFHYANYPQEMPU-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 241000218645 Cedrus Species 0.000 description 1
- NPBVQXIMTZKSBA-UHFFFAOYSA-N Chavibetol Natural products COC1=CC=C(CC=C)C=C1O NPBVQXIMTZKSBA-UHFFFAOYSA-N 0.000 description 1
- 244000223760 Cinnamomum zeylanicum Species 0.000 description 1
- WTEVQBCEXWBHNA-UHFFFAOYSA-N Citral Natural products CC(C)=CCCC(C)=CC=O WTEVQBCEXWBHNA-UHFFFAOYSA-N 0.000 description 1
- 241000402754 Erythranthe moschata Species 0.000 description 1
- 239000005770 Eugenol Substances 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- 241000147041 Guaiacum officinale Species 0.000 description 1
- 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 1
- BJIOGJUNALELMI-ONEGZZNKSA-N Isoeugenol Natural products COC1=CC(\C=C\C)=CC=C1O BJIOGJUNALELMI-ONEGZZNKSA-N 0.000 description 1
- 235000010254 Jasminum officinale Nutrition 0.000 description 1
- 240000005385 Jasminum sambac Species 0.000 description 1
- 240000007472 Leucaena leucocephala Species 0.000 description 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
- 244000062730 Melissa officinalis Species 0.000 description 1
- 235000010654 Melissa officinalis Nutrition 0.000 description 1
- 235000006679 Mentha X verticillata Nutrition 0.000 description 1
- 235000002899 Mentha suaveolens Nutrition 0.000 description 1
- 235000001636 Mentha x rotundifolia Nutrition 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- UVMRYBDEERADNV-UHFFFAOYSA-N Pseudoeugenol Natural products COC1=CC(C(C)=C)=CC=C1O UVMRYBDEERADNV-UHFFFAOYSA-N 0.000 description 1
- 244000297179 Syringa vulgaris Species 0.000 description 1
- 235000004338 Syringa vulgaris Nutrition 0.000 description 1
- 229940022663 acetate Drugs 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- JKRWZLOCPLZZEI-UHFFFAOYSA-N alpha-Trichloromethylbenzyl acetate Chemical compound CC(=O)OC(C(Cl)(Cl)Cl)C1=CC=CC=C1 JKRWZLOCPLZZEI-UHFFFAOYSA-N 0.000 description 1
- GUUHFMWKWLOQMM-NTCAYCPXSA-N alpha-hexylcinnamaldehyde Chemical compound CCCCCC\C(C=O)=C/C1=CC=CC=C1 GUUHFMWKWLOQMM-NTCAYCPXSA-N 0.000 description 1
- UZFLPKAIBPNNCA-BQYQJAHWSA-N alpha-ionone Chemical compound CC(=O)\C=C\C1C(C)=CCCC1(C)C UZFLPKAIBPNNCA-BQYQJAHWSA-N 0.000 description 1
- UZFLPKAIBPNNCA-UHFFFAOYSA-N alpha-ionone Natural products CC(=O)C=CC1C(C)=CCCC1(C)C UZFLPKAIBPNNCA-UHFFFAOYSA-N 0.000 description 1
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- WUOACPNHFRMFPN-UHFFFAOYSA-N alpha-terpineol Chemical compound CC1=CCC(C(C)(C)O)CC1 WUOACPNHFRMFPN-UHFFFAOYSA-N 0.000 description 1
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- 239000006227 byproduct Substances 0.000 description 1
- SVURIXNDRWRAFU-OGMFBOKVSA-N cedrol Chemical compound C1[C@]23[C@H](C)CC[C@H]3C(C)(C)[C@@H]1[C@@](O)(C)CC2 SVURIXNDRWRAFU-OGMFBOKVSA-N 0.000 description 1
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- 239000007795 chemical reaction product Substances 0.000 description 1
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
- 150000001845 chromium compounds Chemical class 0.000 description 1
- 235000017803 cinnamon Nutrition 0.000 description 1
- BJIOGJUNALELMI-ARJAWSKDSA-N cis-isoeugenol Chemical compound COC1=CC(\C=C/C)=CC=C1O BJIOGJUNALELMI-ARJAWSKDSA-N 0.000 description 1
- 229940043350 citral Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- KSMVZQYAVGTKIV-UHFFFAOYSA-N decanal Chemical compound CCCCCCCCCC=O KSMVZQYAVGTKIV-UHFFFAOYSA-N 0.000 description 1
- SQIFACVGCPWBQZ-UHFFFAOYSA-N delta-terpineol Natural products CC(C)(O)C1CCC(=C)CC1 SQIFACVGCPWBQZ-UHFFFAOYSA-N 0.000 description 1
- SOCTUWSJJQCPFX-UHFFFAOYSA-N dichromate(2-) Chemical compound [O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O SOCTUWSJJQCPFX-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
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- 229960004279 formaldehyde Drugs 0.000 description 1
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- WTEVQBCEXWBHNA-JXMROGBWSA-N geranial Chemical compound CC(C)=CCC\C(C)=C\C=O WTEVQBCEXWBHNA-JXMROGBWSA-N 0.000 description 1
- 229940091561 guaiac Drugs 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
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- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- SVURIXNDRWRAFU-UHFFFAOYSA-N juniperanol Natural products C1C23C(C)CCC3C(C)(C)C1C(O)(C)CC2 SVURIXNDRWRAFU-UHFFFAOYSA-N 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- UWKAYLJWKGQEPM-UHFFFAOYSA-N linalool acetate Natural products CC(C)=CCCC(C)(C=C)OC(C)=O UWKAYLJWKGQEPM-UHFFFAOYSA-N 0.000 description 1
- 239000000865 liniment Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 229940100595 phenylacetaldehyde Drugs 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
- 239000003279 phenylacetic acid Substances 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- SATCULPHIDQDRE-UHFFFAOYSA-N piperonal Chemical compound O=CC1=CC=C2OCOC2=C1 SATCULPHIDQDRE-UHFFFAOYSA-N 0.000 description 1
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- 150000007659 semicarbazones Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
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- BJIOGJUNALELMI-UHFFFAOYSA-N trans-isoeugenol Natural products COC1=CC(C=CC)=CC=C1O BJIOGJUNALELMI-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0026—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
- C11B9/0034—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing six 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
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
- C07C45/292—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups with chromium derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/29—Saturated compounds containing keto groups bound to rings
- C07C49/303—Saturated compounds containing keto groups bound to rings to a six-membered ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Fats And Perfumes (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US72806368A | 1968-05-09 | 1968-05-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1923223A1 true DE1923223A1 (de) | 1969-11-20 |
Family
ID=24925258
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19691923223 Pending DE1923223A1 (de) | 1968-05-09 | 1969-05-07 | Derivate des 1-AEthyl-3,3-dimethyl-cyclo-hexans und Verfahren zu deren Herstellung |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE732205A (zh) |
| DE (1) | DE1923223A1 (zh) |
| ES (1) | ES366943A1 (zh) |
| FR (1) | FR2008167A1 (zh) |
| NL (1) | NL6907053A (zh) |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2380776A1 (fr) * | 1976-12-23 | 1978-09-15 | Henkel Kgaa | Utilisation des isomeres cis- et trans- de l'oxyde de 3,3,5-trimethyl-cyclohexyle et d'ethyle et de leurs melanges comme matieres aromatiques et compositions de parfums en contenant |
| WO1998007407A1 (en) * | 1996-08-19 | 1998-02-26 | The Procter & Gamble Company | Fragrance delivery systems for personal care articles |
| WO2000014051A1 (en) * | 1998-09-09 | 2000-03-16 | Firmenich Sa | Esters with musky odor and their use in perfumery |
| US6083892A (en) * | 1997-08-19 | 2000-07-04 | The Procter & Gamble Company | Automatic dishwashing detergents comprising β-ketoester pro-fragrances |
| US6093691A (en) * | 1996-08-19 | 2000-07-25 | The Procter & Gamble Company | Rinse added fabric softening compositions and method of use for the delivery of fragrance derivatives |
| US6100233A (en) * | 1996-08-19 | 2000-08-08 | The Procter & Gamble Company | Odor control compositions comprising β-ketoester pro-fragrances |
| US6126953A (en) * | 1996-08-19 | 2000-10-03 | The Procter & Gamble Company | Fragrance delivery systems for personal care articles |
| US6384269B1 (en) | 1999-08-25 | 2002-05-07 | Firmenich Sa | Esters with musky odor and their use in perfumery |
| EP1452531A1 (en) * | 2003-02-24 | 2004-09-01 | Firmenich Sa | Perfuming ingredient with a floral character |
| WO2020098901A1 (de) | 2018-11-12 | 2020-05-22 | Symrise Ag | Verwendung von 1-ethyl-4,4-dimethyl-cyclohexan-derivaten als duftstoffe |
| WO2023021063A1 (en) * | 2021-08-20 | 2023-02-23 | Basf Se | Use of 1-(4- tert- butyl cyclohexyl) propyl acetate as aroma ingredient |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10214675A1 (de) * | 2002-04-03 | 2003-10-16 | Haarmann & Reimer Gmbh | Neue alicyclische Ester mit Moschusgeruch |
| US6774260B2 (en) * | 2002-09-14 | 2004-08-10 | International Flavors & Fragrances Inc. | Fruity musk compositions |
| BRPI0816731A2 (pt) * | 2007-09-07 | 2015-03-10 | Givaudan Sa | Derivados de dimetilciclo-hexil como neutralizadores de mau odor |
| FR2959738B1 (fr) | 2010-05-05 | 2012-05-11 | Mane Fils V | Composes a la note boisee. |
| EP2632554B1 (en) | 2010-10-25 | 2017-01-04 | Symrise AG | Perfume |
| WO2020125993A1 (en) * | 2018-12-20 | 2020-06-25 | Symrise Ag | Alicyclic musk fragrance compounds |
| EP4132901A1 (en) * | 2020-04-08 | 2023-02-15 | Symrise AG | Esters as fragrance compounds |
-
1969
- 1969-04-28 BE BE732205D patent/BE732205A/xx unknown
- 1969-05-07 DE DE19691923223 patent/DE1923223A1/de active Pending
- 1969-05-08 NL NL6907053A patent/NL6907053A/xx unknown
- 1969-05-08 ES ES366943A patent/ES366943A1/es not_active Expired
- 1969-05-09 FR FR6915025A patent/FR2008167A1/fr not_active Withdrawn
Cited By (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2380776A1 (fr) * | 1976-12-23 | 1978-09-15 | Henkel Kgaa | Utilisation des isomeres cis- et trans- de l'oxyde de 3,3,5-trimethyl-cyclohexyle et d'ethyle et de leurs melanges comme matieres aromatiques et compositions de parfums en contenant |
| WO1998007814A2 (en) * | 1996-08-19 | 1998-02-26 | The Procter & Gamble Company | Fragrance delivery system for liquid detergent compositions |
| WO1998007405A1 (en) * | 1996-08-19 | 1998-02-26 | The Procter & Gamble Company | Fragrance delivery systems |
| WO1998007455A1 (en) * | 1996-08-19 | 1998-02-26 | The Procter & Gamble Company | ODOR CONTROL COMPOSITIONS COMPRISING β-KETOESTER PRO-FRAGRANCES |
| US6184188B1 (en) | 1996-08-19 | 2001-02-06 | The Procter & Gamble Company | Fragrance delivery system for liquid detergent compositions |
| WO1998007812A3 (en) * | 1996-08-19 | 1998-03-26 | Procter & Gamble | AUTOMATIC DISHWASHING DETERGENTS COMPRISING β-KETOESTER PRO-FRAGRANCES |
| WO1998007813A2 (en) * | 1996-08-19 | 1998-02-26 | The Procter & Gamble Company | LAUNDRY DETERGENT COMPOSITIONS COMPRISING β-KETOESTER PRO-FRAGRANCES |
| WO1998007812A2 (en) * | 1996-08-19 | 1998-02-26 | The Procter & Gamble Company | AUTOMATIC DISHWASHING DETERGENTS COMPRISING β-KETOESTER PRO-FRAGRANCES |
| WO1998007814A3 (en) * | 1996-08-19 | 1998-03-26 | Procter & Gamble | Fragrance delivery system for liquid detergent compositions |
| WO1998007809A2 (en) * | 1996-08-19 | 1998-02-26 | The Procter & Gamble Company | HARD SURFACE CLEANERS COMPRISING β-KETOESTER PRO-FRAGRANCES |
| WO1998007809A3 (en) * | 1996-08-19 | 1998-05-07 | Procter & Gamble | HARD SURFACE CLEANERS COMPRISING β-KETOESTER PRO-FRAGRANCES |
| WO1998007813A3 (en) * | 1996-08-19 | 1998-05-14 | Procter & Gamble | LAUNDRY DETERGENT COMPOSITIONS COMPRISING β-KETOESTER PRO-FRAGRANCES |
| WO1998007407A1 (en) * | 1996-08-19 | 1998-02-26 | The Procter & Gamble Company | Fragrance delivery systems for personal care articles |
| US6126953A (en) * | 1996-08-19 | 2000-10-03 | The Procter & Gamble Company | Fragrance delivery systems for personal care articles |
| US6093691A (en) * | 1996-08-19 | 2000-07-25 | The Procter & Gamble Company | Rinse added fabric softening compositions and method of use for the delivery of fragrance derivatives |
| US6100233A (en) * | 1996-08-19 | 2000-08-08 | The Procter & Gamble Company | Odor control compositions comprising β-ketoester pro-fragrances |
| US6083892A (en) * | 1997-08-19 | 2000-07-04 | The Procter & Gamble Company | Automatic dishwashing detergents comprising β-ketoester pro-fragrances |
| WO2000014051A1 (en) * | 1998-09-09 | 2000-03-16 | Firmenich Sa | Esters with musky odor and their use in perfumery |
| USRE38659E1 (en) * | 1998-09-09 | 2004-11-23 | Firmenich Sa | Esters with musky odor and their use in perfumery |
| US6384269B1 (en) | 1999-08-25 | 2002-05-07 | Firmenich Sa | Esters with musky odor and their use in perfumery |
| EP1452531A1 (en) * | 2003-02-24 | 2004-09-01 | Firmenich Sa | Perfuming ingredient with a floral character |
| US7189688B2 (en) | 2003-02-24 | 2007-03-13 | Firmenich Sa | Perfuming ingredient with a floral character |
| WO2020098901A1 (de) | 2018-11-12 | 2020-05-22 | Symrise Ag | Verwendung von 1-ethyl-4,4-dimethyl-cyclohexan-derivaten als duftstoffe |
| CN112969444A (zh) * | 2018-11-12 | 2021-06-15 | 西姆莱斯有限公司 | 1-乙基-4，4-二甲基环己烷衍生物作为香味物质的用途 |
| US11946019B2 (en) | 2018-11-12 | 2024-04-02 | Symrise Ag | Synthesis and use of 2-ethyl-5,5-dimethyl-cyclohexanol as fragrance and flavor material |
| US12031106B2 (en) | 2018-11-12 | 2024-07-09 | Symrise Ag | Use of 1-ethyl-4,4-dimethyl-cyclohexane derivatives as fragrances |
| WO2023021063A1 (en) * | 2021-08-20 | 2023-02-23 | Basf Se | Use of 1-(4- tert- butyl cyclohexyl) propyl acetate as aroma ingredient |
Also Published As
| Publication number | Publication date |
|---|---|
| ES366943A1 (es) | 1971-03-16 |
| NL6907053A (zh) | 1969-11-11 |
| BE732205A (zh) | 1969-10-28 |
| FR2008167A1 (fr) | 1970-01-16 |
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