DE1593442C - - Google Patents
Info
- Publication number
- DE1593442C DE1593442C DE19661593442 DE1593442A DE1593442C DE 1593442 C DE1593442 C DE 1593442C DE 19661593442 DE19661593442 DE 19661593442 DE 1593442 A DE1593442 A DE 1593442A DE 1593442 C DE1593442 C DE 1593442C
- Authority
- DE
- Germany
- Prior art keywords
- acetyl
- tetramethyl
- enol
- formula
- boiling point
- 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
Links
- 125000005594 diketone group Chemical group 0.000 claims description 6
- 238000009835 boiling Methods 0.000 description 23
- -1 1-Ethoxy vinyl Chemical group 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 239000000203 mixture Substances 0.000 description 13
- UCXHCWOVLRUIMX-UHFFFAOYSA-N 1-[2,2,6,6-tetramethyl-4-(3-methylbutoxy)cyclohex-3-en-1-yl]ethanone Chemical compound CC(C)CCOC1=CC(C)(C)C(C(C)=O)C(C)(C)C1 UCXHCWOVLRUIMX-UHFFFAOYSA-N 0.000 description 12
- 150000002084 enol ethers Chemical class 0.000 description 12
- 230000000875 corresponding Effects 0.000 description 11
- KZMGYPLQYOPHEL-UHFFFAOYSA-N ethoxyethane;trifluoroborane Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 11
- 125000002587 enol group Chemical group 0.000 description 10
- OZXIZRZFGJZWBF-UHFFFAOYSA-N 1,3,5-trimethyl-2-(2,4,6-trimethylphenoxy)benzene Chemical compound CC1=CC(C)=CC(C)=C1OC1=C(C)C=C(C)C=C1C OZXIZRZFGJZWBF-UHFFFAOYSA-N 0.000 description 9
- 125000004432 carbon atoms Chemical group C* 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 238000000034 method Methods 0.000 description 7
- PYOKUURKVVELLB-UHFFFAOYSA-N Trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 230000035943 smell Effects 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 239000002841 Lewis acid Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 150000002576 ketones Chemical class 0.000 description 5
- 150000007517 lewis acids Chemical class 0.000 description 5
- BFDXJNAUFLSGBZ-UHFFFAOYSA-N 4-acetyl-3,3,5,5-tetramethylcyclohexan-1-one Chemical compound CC(=O)C1C(C)(C)CC(=O)CC1(C)C BFDXJNAUFLSGBZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating Effects 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 125000003500 enol ether group Chemical group 0.000 description 4
- 150000002170 ethers Chemical class 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- GKGFTIKPKGWMOW-UHFFFAOYSA-N propane-1,1,1-triolate Chemical group CCC([O-])([O-])[O-] GKGFTIKPKGWMOW-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- YLNYLLVKHRZLGO-UHFFFAOYSA-N 4-(1-ethoxyethenyl)-3,3,5,5-tetramethylcyclohexan-1-one Chemical compound CCOC(=C)C1C(C)(C)CC(=O)CC1(C)C YLNYLLVKHRZLGO-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000003205 fragrance Substances 0.000 description 3
- 238000005907 ketalization reaction Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000001187 sodium carbonate Substances 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- ARMBXTPLUPASTA-UHFFFAOYSA-N (4-acetyl-3,3,5,5-tetramethylcyclohexen-1-yl) acetate Chemical compound CC(=O)OC1=CC(C)(C)C(C(C)=O)C(C)(C)C1 ARMBXTPLUPASTA-UHFFFAOYSA-N 0.000 description 2
- AUCXIGOESXVILY-UHFFFAOYSA-N 1,2,3,3-tetramethylcyclohexene Chemical compound CC1=C(C)C(C)(C)CCC1 AUCXIGOESXVILY-UHFFFAOYSA-N 0.000 description 2
- IGRURXZWJCSNKU-UHFFFAOYSA-M 3-methylbut-3-enoate Chemical compound CC(=C)CC([O-])=O IGRURXZWJCSNKU-UHFFFAOYSA-M 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N Cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N P-Toluenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 235000016639 Syzygium aromaticum Nutrition 0.000 description 2
- 240000005147 Syzygium aromaticum Species 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000007799 cork Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 238000006266 etherification reaction Methods 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- 239000008079 hexane Substances 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- SAGMWIOLIVLWKW-UHFFFAOYSA-N 1-(2,2,6,6-tetramethyl-4,4-dipropoxycyclohexyl)ethanone Chemical compound CCCOC1(OCCC)CC(C)(C)C(C(C)=O)C(C)(C)C1 SAGMWIOLIVLWKW-UHFFFAOYSA-N 0.000 description 1
- CRQPNSIAKUWXBO-UHFFFAOYSA-N 1-(4,4-dibutoxy-2,2,6,6-tetramethylcyclohexyl)ethanone Chemical compound CCCCOC1(OCCCC)CC(C)(C)C(C(C)=O)C(C)(C)C1 CRQPNSIAKUWXBO-UHFFFAOYSA-N 0.000 description 1
- MDIXEIPKOGLAPR-UHFFFAOYSA-N 1-(4,4-dimethoxy-2,2,6,6-tetramethylcyclohexyl)ethanone Chemical compound COC1(OC)CC(C)(C)C(C(C)=O)C(C)(C)C1 MDIXEIPKOGLAPR-UHFFFAOYSA-N 0.000 description 1
- OVRLIQFCLQOCRB-UHFFFAOYSA-N 1-(4-ethoxy-2,2,6,6-tetramethylcyclohex-3-en-1-yl)ethanone Chemical compound CCOC1=CC(C)(C)C(C(C)=O)C(C)(C)C1 OVRLIQFCLQOCRB-UHFFFAOYSA-N 0.000 description 1
- AKQOWURCNQEVNF-UHFFFAOYSA-N 1-(7,7,9,9-tetramethyl-1,4-dioxaspiro[4.5]decan-8-yl)ethanone Chemical compound C1C(C)(C)C(C(=O)C)C(C)(C)CC21OCCO2 AKQOWURCNQEVNF-UHFFFAOYSA-N 0.000 description 1
- MEZUBVMPZHGTTQ-UHFFFAOYSA-N 1-[2,2,6,6-tetramethyl-4,4-bis(2-methylpropoxy)cyclohexyl]ethanone Chemical compound CC(C)COC1(OCC(C)C)CC(C)(C)C(C(C)=O)C(C)(C)C1 MEZUBVMPZHGTTQ-UHFFFAOYSA-N 0.000 description 1
- CPBZARXQRZTYGI-UHFFFAOYSA-N 3-cyclopentylpropylcyclohexane Chemical compound C1CCCCC1CCCC1CCCC1 CPBZARXQRZTYGI-UHFFFAOYSA-N 0.000 description 1
- YJXXLBNAJPSMRZ-UHFFFAOYSA-N CC(C)CCOC([O-])[O-] Chemical compound CC(C)CCOC([O-])[O-] YJXXLBNAJPSMRZ-UHFFFAOYSA-N 0.000 description 1
- CQLXXUDBMWXSLW-UHFFFAOYSA-N CC(C)COC([O-])[O-] Chemical compound CC(C)COC([O-])[O-] CQLXXUDBMWXSLW-UHFFFAOYSA-N 0.000 description 1
- HCONIDJXUXYDSN-UHFFFAOYSA-N CCCOC([O-])[O-] Chemical compound CCCOC([O-])[O-] HCONIDJXUXYDSN-UHFFFAOYSA-N 0.000 description 1
- YSQXQZWCWSBCJH-UHFFFAOYSA-N COC(=C)C1C(CC(CC1(C)C)=O)(C)C Chemical compound COC(=C)C1C(CC(CC1(C)C)=O)(C)C YSQXQZWCWSBCJH-UHFFFAOYSA-N 0.000 description 1
- HGCIXCUEYOPUTN-UHFFFAOYSA-N Cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 241000208152 Geranium Species 0.000 description 1
- 240000000513 Santalum album Species 0.000 description 1
- 235000008632 Santalum album Nutrition 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- IMROMDMJAWUWLK-UHFFFAOYSA-N ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- FUQAYSQLAOJBBC-UHFFFAOYSA-N β-Caryophyllene alcohol Chemical compound C1CC(C2)(C)CCCC2(O)C2CC(C)(C)C21 FUQAYSQLAOJBBC-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1421665 | 1965-10-14 | ||
| CH1421665A CH467333A (fr) | 1965-10-14 | 1965-10-14 | Utilisation de dicétones comme odorants dans la préparation de compositions parfumées |
| DES0106442 | 1966-10-11 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1593442A1 DE1593442A1 (de) | 1970-07-16 |
| DE1593442C true DE1593442C (xx) | 1973-04-05 |
Family
ID=4398919
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661593442 Granted DE1593442A1 (de) | 1965-10-14 | 1966-10-11 | Verfahren zur Herstellung von cyclischen Verbindungen |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3578715A (xx) |
| BE (1) | BE687954A (xx) |
| CH (1) | CH467333A (xx) |
| DE (1) | DE1593442A1 (xx) |
| DK (1) | DK136191B (xx) |
| ES (1) | ES332218A0 (xx) |
| FR (1) | FR1498736A (xx) |
| GB (1) | GB1141910A (xx) |
| NL (1) | NL6614506A (xx) |
| SE (1) | SE352619B (xx) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3875241A (en) * | 1965-10-14 | 1975-04-01 | Roure Bertrand Dupont Sa | Bis-enolethers of substituted acetyl cyclohexanones |
| US3953516A (en) * | 1965-10-14 | 1976-04-27 | Societe Anonyme Roure Bertrand Dupont | Mono-enol ethers of 4-acetyl-3,3,5,5-tetramethylcyclohexanone |
| US3953471A (en) * | 1965-10-14 | 1976-04-27 | Societe Anonyme Roure Bertrand Dupont | Ketals of 4-acetyl-3,3,5,5-tetramethylcyclohexanone |
| US3953515A (en) * | 1965-10-14 | 1976-04-27 | Societe Anonyme Roure Bertrand Dupont | 4-Acetyl-3,3,5,5 tetraalkylcyclohexanones |
| US3948815A (en) * | 1965-10-14 | 1976-04-06 | Bernard Pierre Corbier | Perfume compositions |
| US3927107A (en) * | 1972-10-26 | 1975-12-16 | Firmenich & Cie | 2,6,6-Trimethyl-1-alkenoyl-cyclohexenones |
| GB1390654A (en) * | 1972-10-26 | 1975-04-16 | Beheer Bv Pfw | Materials for flavours and perfumes and process therefor |
| US4084009A (en) * | 1977-03-03 | 1978-04-11 | International Flavors & Fragrances Inc. | Flavoring with a hydroxy cyclohexenone derivative |
| US4788337A (en) * | 1988-01-28 | 1988-11-29 | International Flavors & Fragrances Inc. | 2-alkanoyl-2-(1-penten-1-yl)cyclohexanones, process for preparing same, and organoleptic uses thereof and intermediates useful in said process |
| US10858304B1 (en) * | 2019-09-04 | 2020-12-08 | Eastman Chemical Company | Aromatic enol ethers |
-
1965
- 1965-10-14 CH CH1421665A patent/CH467333A/fr unknown
-
1966
- 1966-10-07 BE BE687954D patent/BE687954A/xx unknown
- 1966-10-10 US US585259A patent/US3578715A/en not_active Expired - Lifetime
- 1966-10-11 DE DE19661593442 patent/DE1593442A1/de active Granted
- 1966-10-12 FR FR79588A patent/FR1498736A/fr not_active Expired
- 1966-10-13 ES ES332218A patent/ES332218A0/es active Pending
- 1966-10-13 GB GB45844/66A patent/GB1141910A/en not_active Expired
- 1966-10-14 DK DK532966AA patent/DK136191B/da unknown
- 1966-10-14 NL NL6614506A patent/NL6614506A/xx unknown
- 1966-10-14 SE SE13968/66A patent/SE352619B/xx unknown
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