CH616077A5 - - Google Patents
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- Publication number
- CH616077A5 CH616077A5 CH834376A CH834376A CH616077A5 CH 616077 A5 CH616077 A5 CH 616077A5 CH 834376 A CH834376 A CH 834376A CH 834376 A CH834376 A CH 834376A CH 616077 A5 CH616077 A5 CH 616077A5
- Authority
- CH
- Switzerland
- Prior art keywords
- formula
- compounds
- methyl
- cyclopentylidene
- acetate
- Prior art date
Links
- 239000000203 mixture Substances 0.000 claims description 12
- 239000004615 ingredient Substances 0.000 claims description 5
- 150000001334 alicyclic compounds Chemical class 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 229930195734 saturated hydrocarbon Natural products 0.000 claims 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 16
- KQENDZXFFPZPFV-UHFFFAOYSA-N cyclopentylidenemethyl acetate Chemical compound CC(=O)OC=C1CCCC1 KQENDZXFFPZPFV-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000002304 perfume Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- -1 t-butyl cyclopen-tylidene acetates Chemical class 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 240000007436 Cananga odorata Species 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- YKYONYBAUNKHLG-UHFFFAOYSA-N propyl acetate Chemical class CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- GGFUQEDJNKQRBK-UHFFFAOYSA-N C(C)(=O)OCC=C1CCCC1 Chemical compound C(C)(=O)OCC=C1CCCC1 GGFUQEDJNKQRBK-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- BGTOWKSIORTVQH-HOSYLAQJSA-N cyclopentanone Chemical class O=[13C]1CCCC1 BGTOWKSIORTVQH-HOSYLAQJSA-N 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- QABLOFMHHSOFRJ-UHFFFAOYSA-N methyl 2-chloroacetate Chemical compound COC(=O)CCl QABLOFMHHSOFRJ-UHFFFAOYSA-N 0.000 description 2
- SIGOIUCRXKUEIG-UHFFFAOYSA-N methyl 2-dimethoxyphosphorylacetate Chemical compound COC(=O)CP(=O)(OC)OC SIGOIUCRXKUEIG-UHFFFAOYSA-N 0.000 description 2
- KVWWIYGFBYDJQC-UHFFFAOYSA-N methyl dihydrojasmonate Chemical compound CCCCCC1C(CC(=O)OC)CCC1=O KVWWIYGFBYDJQC-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 230000000630 rising effect Effects 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical group COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 2
- GDIYABNICDPBCR-UHFFFAOYSA-N (1-tert-butylcyclohexyl) acetate Chemical compound CC(=O)OC1(C(C)(C)C)CCCCC1 GDIYABNICDPBCR-UHFFFAOYSA-N 0.000 description 1
- QMVPMAAFGQKVCJ-SNVBAGLBSA-N (R)-(+)-citronellol Natural products OCC[C@H](C)CCC=C(C)C QMVPMAAFGQKVCJ-SNVBAGLBSA-N 0.000 description 1
- MINJGYRWHNAENM-UHFFFAOYSA-N 2,5,9-trimethyldeca-4,9-dienal Chemical compound O=CC(C)CC=C(C)CCCC(C)=C MINJGYRWHNAENM-UHFFFAOYSA-N 0.000 description 1
- FZPZQBMVJQQHIJ-UHFFFAOYSA-N 3,5-dimethylhept-4-enal Chemical compound CC(CC=O)C=C(CC)C FZPZQBMVJQQHIJ-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
- IKTHMQYJOWTSJO-UHFFFAOYSA-N 4-Acetyl-6-tert-butyl-1,1-dimethylindane Chemical compound CC(=O)C1=CC(C(C)(C)C)=CC2=C1CCC2(C)C IKTHMQYJOWTSJO-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 241000746418 Dalbergia nigra Species 0.000 description 1
- 238000006546 Horner-Wadsworth-Emmons reaction Methods 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
- 235000010254 Jasminum officinale Nutrition 0.000 description 1
- 240000005385 Jasminum sambac Species 0.000 description 1
- XMLSXPIVAXONDL-PLNGDYQASA-N Jasmone Chemical compound CC\C=C/CC1=C(C)CCC1=O XMLSXPIVAXONDL-PLNGDYQASA-N 0.000 description 1
- 244000178870 Lavandula angustifolia Species 0.000 description 1
- 235000010663 Lavandula angustifolia Nutrition 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 238000007239 Wittig reaction Methods 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- JGQFVRIQXUFPAH-UHFFFAOYSA-N beta-citronellol Natural products OCCC(C)CCCC(C)=C JGQFVRIQXUFPAH-UHFFFAOYSA-N 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- IVLCENBZDYVJPA-ARJAWSKDSA-N cis-Jasmone Natural products C\C=C/CC1=C(C)CCC1=O IVLCENBZDYVJPA-ARJAWSKDSA-N 0.000 description 1
- 235000000484 citronellol Nutrition 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000001102 lavandula vera Substances 0.000 description 1
- 235000018219 lavender Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229940067107 phenylethyl alcohol Drugs 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- XMLSXPIVAXONDL-UHFFFAOYSA-N trans-jasmone Natural products CCC=CCC1=C(C)CCC1=O XMLSXPIVAXONDL-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 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
- C11B9/003—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing less than six carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
- Cosmetics (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH834376A CH616077A5 (de) | 1976-06-30 | 1976-06-30 | |
| DE2729121A DE2729121C3 (de) | 1976-06-30 | 1977-06-28 | Verwendung von Cyclopentanderivaten als Riechstoffe und neue Cyclopentanderivaten |
| FR7719883A FR2397187A1 (fr) | 1976-06-30 | 1977-06-28 | Composition parfumante a base d'ester de cyclopentylidene et son utilisation |
| NL7707200A NL7707200A (nl) | 1976-06-30 | 1977-06-29 | Werkwijze ter bereiding van cyclopentaanderi- vaten. |
| JP7770577A JPS533541A (en) | 1976-06-30 | 1977-06-29 | Method of modifying emphasizing or changing smell characteristics of scent or scenttgiving product and basic agent of perfume |
| GB27496/77A GB1531946A (en) | 1976-06-30 | 1977-06-30 | Cyclopentane derivatives useful as perfuming agents |
| US06/104,404 US4280934A (en) | 1976-06-30 | 1979-02-17 | Cyclopentane derivatives useful as perfuming agents |
| US06/245,519 US4338458A (en) | 1976-06-30 | 1981-03-19 | Cyclopentane derivatives useful as perfuming agents |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH834376A CH616077A5 (de) | 1976-06-30 | 1976-06-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH616077A5 true CH616077A5 (de) | 1980-03-14 |
Family
ID=4338865
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH834376A CH616077A5 (de) | 1976-06-30 | 1976-06-30 |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US4280934A (de) |
| JP (1) | JPS533541A (de) |
| CH (1) | CH616077A5 (de) |
| DE (1) | DE2729121C3 (de) |
| FR (1) | FR2397187A1 (de) |
| GB (1) | GB1531946A (de) |
| NL (1) | NL7707200A (de) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4390718A (en) * | 1981-07-01 | 1983-06-28 | Hoffmann-La Roche Inc. | Prostaglandin intermediates |
| DE3216440A1 (de) * | 1982-05-03 | 1983-11-03 | Skf Kugellagerfabriken Gmbh | Kugellager fuer laengs- und drehbewegungen |
| DE3469562D1 (en) * | 1983-01-26 | 1988-04-07 | Firmenich & Cie | Use of 1-cyclopentenylacetic acid as perfuming ingredient, perfuming composition containing it and perfumed products |
| HU193546B (en) * | 1983-12-21 | 1987-10-28 | Egyt Gyogyszervegyeszeti Gyar | Process for production of derivatives of 3,5-ethan-2,4-dedecadiene acid |
| DE69505226T2 (de) * | 1994-06-23 | 1999-03-25 | Firmenich S.A., Genf/Geneve | Verfahren zur herstellung von (+)-(1r)-cis-3-oxo-2-pentyl-1-cyclopentanessigsäure |
| ES2216757T3 (es) | 1999-07-05 | 2004-11-01 | Givaudan Sa | Ciclopentilalquilnitrilos yel uso de derivados de ciclopentilalquilo odoriferos como fragancias. |
| NL1027741C2 (nl) * | 2004-12-14 | 2006-06-16 | Denka Internat Holding B V | Werkwijze voor het remmen van hoedopening en/of bruin worden bij eetbare paddestoelen. |
| EP2474301B1 (de) * | 2011-12-14 | 2014-04-16 | Symrise AG | Riechstoffmischungen enthaltend Cyclopent-2-Enyl-Essigsäureethylester |
| US10876067B2 (en) | 2016-02-15 | 2020-12-29 | Symrise Ag | Fragrant mixtures containing esters and ketones |
| CN106397482A (zh) * | 2016-08-30 | 2017-02-15 | 江西盛伟科技股份有限公司 | 一种膦酰基乙酸三甲酯的合成方法 |
| CN111744445A (zh) * | 2020-07-20 | 2020-10-09 | 江西盛伟科技股份有限公司 | 一种乙基磷酰基乙酸二甲酯的制备装置及合成工艺 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1965792A (en) * | 1931-03-06 | 1934-07-10 | Cie De Bethune | Esters of unsubstituted and alphasubstituted cyclopentenylacetic acid and their production |
| GB723703A (en) * | 1953-08-17 | 1955-02-09 | John B Pillin Ltd | Improvements in or relating to releasable ratchet mechanism |
| US2907534A (en) * | 1955-03-08 | 1959-10-06 | Stewart Warner Corp | Hose reel |
| US3997586A (en) * | 1967-08-22 | 1976-12-14 | Roussel-Uclaf | Cyclopropanecarboxylic acids and esters |
-
1976
- 1976-06-30 CH CH834376A patent/CH616077A5/fr not_active IP Right Cessation
-
1977
- 1977-06-28 FR FR7719883A patent/FR2397187A1/fr active Granted
- 1977-06-28 DE DE2729121A patent/DE2729121C3/de not_active Expired
- 1977-06-29 JP JP7770577A patent/JPS533541A/ja active Granted
- 1977-06-29 NL NL7707200A patent/NL7707200A/xx not_active Application Discontinuation
- 1977-06-30 GB GB27496/77A patent/GB1531946A/en not_active Expired
-
1979
- 1979-02-17 US US06/104,404 patent/US4280934A/en not_active Expired - Lifetime
-
1981
- 1981-03-19 US US06/245,519 patent/US4338458A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| FR2397187B1 (de) | 1983-06-10 |
| FR2397187A1 (fr) | 1979-02-09 |
| DE2729121A1 (de) | 1978-01-12 |
| JPS5437209B2 (de) | 1979-11-14 |
| JPS533541A (en) | 1978-01-13 |
| DE2729121B2 (de) | 1980-04-24 |
| GB1531946A (en) | 1978-11-15 |
| NL7707200A (nl) | 1978-01-03 |
| US4280934A (en) | 1981-07-28 |
| DE2729121C3 (de) | 1981-01-15 |
| US4338458A (en) | 1982-07-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |