DE2753644C2 - Cyclopentane derivatives, process for their preparation and their use - Google Patents
Cyclopentane derivatives, process for their preparation and their useInfo
- Publication number
- DE2753644C2 DE2753644C2 DE19772753644 DE2753644A DE2753644C2 DE 2753644 C2 DE2753644 C2 DE 2753644C2 DE 19772753644 DE19772753644 DE 19772753644 DE 2753644 A DE2753644 A DE 2753644A DE 2753644 C2 DE2753644 C2 DE 2753644C2
- Authority
- DE
- Germany
- Prior art keywords
- cyclopentane derivatives
- preparation
- alkyl radical
- formula
- catalyst
- 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
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 3
- 125000001511 cyclopentyl group Chemical class [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 title claims 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 150000001336 alkenes Chemical class 0.000 claims description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 2
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 6
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000012437 perfumed product Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000007037 hydroformylation reaction Methods 0.000 description 3
- 229910052703 rhodium Inorganic materials 0.000 description 3
- 239000010948 rhodium Substances 0.000 description 3
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 description 2
- OOCCDEMITAIZTP-QPJJXVBHSA-N (E)-cinnamyl alcohol Chemical compound OC\C=C\C1=CC=CC=C1 OOCCDEMITAIZTP-QPJJXVBHSA-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
- CXROTAVXRPCAKF-UHFFFAOYSA-N 3-(3-hydroxy-2,3-dimethylcyclopentyl)butanal Chemical compound O=CCC(C)C1CCC(C)(O)C1C CXROTAVXRPCAKF-UHFFFAOYSA-N 0.000 description 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 2
- 241000755716 Convallaria Species 0.000 description 2
- 235000009046 Convallaria majalis Nutrition 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 description 2
- 150000001728 carbonyl compounds Chemical class 0.000 description 2
- JOZKFWLRHCDGJA-UHFFFAOYSA-N citronellol acetate Chemical compound CC(=O)OCCC(C)CCC=C(C)C JOZKFWLRHCDGJA-UHFFFAOYSA-N 0.000 description 2
- 150000001940 cyclopentanes Chemical class 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 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
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- -1 rhodium carbonyl compound Chemical class 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 229940098795 (3z)- 3-hexenyl acetate Drugs 0.000 description 1
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-Phenylethanol Natural products OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 1
- ZJPKYCLAROITRY-UHFFFAOYSA-N 3-(1-ethoxyethoxy)-3,7-dimethylocta-1,6-diene Chemical compound CCOC(C)OC(C)(C=C)CCC=C(C)C ZJPKYCLAROITRY-UHFFFAOYSA-N 0.000 description 1
- JOZKFWLRHCDGJA-LLVKDONJSA-N Citronellyl acetate Natural products CC(=O)OCC[C@H](C)CCC=C(C)C JOZKFWLRHCDGJA-LLVKDONJSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 241000234435 Lilium Species 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- OOCCDEMITAIZTP-UHFFFAOYSA-N allylic benzylic alcohol Natural products OCC=CC1=CC=CC=C1 OOCCDEMITAIZTP-UHFFFAOYSA-N 0.000 description 1
- WUOACPNHFRMFPN-UHFFFAOYSA-N alpha-terpineol Chemical compound CC1=CCC(C(C)(C)O)CC1 WUOACPNHFRMFPN-UHFFFAOYSA-N 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 229940007550 benzyl acetate Drugs 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- NPFVOOAXDOBMCE-PLNGDYQASA-N cis-3-Hexenyl acetate Natural products CC\C=C/CCOC(C)=O NPFVOOAXDOBMCE-PLNGDYQASA-N 0.000 description 1
- RRGOKSYVAZDNKR-ARJAWSKDSA-M cis-3-hexenylacetate Chemical compound CC\C=C/CCCC([O-])=O RRGOKSYVAZDNKR-ARJAWSKDSA-M 0.000 description 1
- 125000000300 citronellol group Chemical group 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 150000001934 cyclohexanes Chemical class 0.000 description 1
- SQIFACVGCPWBQZ-UHFFFAOYSA-N delta-terpineol Natural products CC(C)(O)C1CCC(=C)CC1 SQIFACVGCPWBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000002781 deodorant agent Substances 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
- 239000002638 heterogeneous catalyst Substances 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- WPFVBOQKRVRMJB-UHFFFAOYSA-N hydroxycitronellal Chemical compound O=CCC(C)CCCC(C)(C)O WPFVBOQKRVRMJB-UHFFFAOYSA-N 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- 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
- UWKAYLJWKGQEPM-UHFFFAOYSA-N linalool acetate Natural products CC(C)=CCCC(C)(C=C)OC(C)=O UWKAYLJWKGQEPM-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229940116411 terpineol Drugs 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 238000004227 thermal cracking Methods 0.000 description 1
- NPFVOOAXDOBMCE-UHFFFAOYSA-N trans-3-hexenyl acetate Natural products CCC=CCCOC(C)=O NPFVOOAXDOBMCE-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
- C11B9/003—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing less than six carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C35/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic
- C07C35/06—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic containing a five-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
- C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/02—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen
- C07C47/19—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen containing hydroxy groups
- C07C47/192—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen containing hydroxy groups containing rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
Die Erfindung betrifft neue Cyclopentan-Derivate, die als chemische Aromastoffe von Interesse sind, Verfahren zu ihrer Herstellung und ihre Verwendung für parfümierte Produkte.The invention relates to new cyclopentane derivatives which are of interest as chemical flavorings, processes for their manufacture and their use in perfumed products.
In der DE-OS 27 35 639 sind Cyclohexan-Derivate der Formel I beschriebenIn DE-OS 27 35 639 cyclohexane derivatives of the formula I are described
Verbindungen ebenfalls als Aromastoffe von Interesse sind.Compounds are also of interest as flavorings.
Gegenstand der Erfindung sind somit Cyclopentan-Derivate der Formel IIThe invention thus relates to cyclopentane derivatives of the formula II
(III)(III)
in der R1, R2, R3 und R4 nach Anspruch 1 definiert sind, in an sich bekannter Weise in Gegenwart einer Metallcarbonylverbindung als Katalysator hydroformyliert. in which R 1 , R 2 , R 3 and R 4 are defined according to claim 1, hydroformylated in a manner known per se in the presence of a metal carbonyl compound as catalyst.
5. Verwendung der Verbindungen nach Anspruch 1 als Aromastoff für parfümierte Produkte.5. Use of the compounds according to claim 1 as a flavoring for perfumed products.
4545
(D(D
CH-CH2CHOCH-CH 2 CHO
R3 R 3
in der R1 ein Alkylrest, R2 und R3 je ein Wasserstoffatom
oder ein Alkylrest, X eine Hydroxylgruppe und Y ein Wasserstoffatom ist oder X und Y zusammen einen
Epoxydrest bilden.
Es wurde nun festgestellt, daß gewisse verwandte R1 in which R 1 is an alkyl radical, R 2 and R 3 are each a hydrogen atom or an alkyl radical, X is a hydroxyl group and Y is a hydrogen atom or X and Y together form an epoxy radical.
It has now been found that certain related R 1
1515th
R2 R 2
ΟΗΟΗ
CH-CH2CHOCH-CH 2 CHO
R3 R 3
(H)(H)
in der R1 und R4 je einen Ci-4-Alkylrest und R2 und R3 je ein Wasserstoffatom oder einen Ci _4-Alkylrest bedeuten. in which R 1 and R 4 each denote a Ci-4-alkyl radical and R 2 and R 3 each denote a hydrogen atom or a Ci -4-alkyl radical.
R1, R2 oder R3 sind insbesondere Methylreste. Vor-20 zugsweise ist einer der Reste R2 oder R3 ein Ci _4-Alkylrest und der andere ein Wasserstoffatom.R 1 , R 2 or R 3 are, in particular, methyl radicals. Preferably, one of the radicals R 2 or R 3 is a C 1-4 alkyl radical and the other is a hydrogen atom.
Eine besonders bevorzugte Verbindung der Formel II ist3-(2,3-Dimethyl-3-hydroxycyclopentyl)-butanal.A particularly preferred compound of the formula II is 3- (2,3-dimethyl-3-hydroxycyclopentyl) butanal.
Die Erfindung betrifft ferner ein Verfahren zur Herstellung der Verbindung der Formel II, das dadurch gekennzeichnet ist, daß man ein Olefin der Formel IIIThe invention also relates to a method of production the compound of the formula II, which is characterized in that an olefin of the formula III
3030th
3535
(IH)(IH)
R2 C = CH2 R 2 C = CH 2
in der R1, R2, R3 und R4 wie in bezug auf Formel II definiert sind, in an sich bekannter Weise in Gegenwart einer Metallcarbonylverbindung als Katalysator hydroformyliert. in which R 1 , R 2 , R 3 and R 4 are as defined in relation to formula II, hydroformylated in a manner known per se in the presence of a metal carbonyl compound as catalyst.
Als Katalysator im erfindungsgemäßen Verfahren geeignet ist eine Kobalt- oder Rhodiumcarbonylverbindung; bevorzugt ist ein Rhodiumcarbonylkomplex, insbesondere ein Komplex, der Hydrid- und/oder Phosphingruppen enthält. Der Katalysator kann homogen sein, wie die Verbindung der FormelA cobalt or rhodium carbonyl compound is suitable as a catalyst in the process according to the invention; A rhodium carbonyl complex is preferred, in particular a complex which is hydride and / or Contains phosphine groups. The catalyst can be homogeneous, like the compound of the formula
HRh(CO)[P(C6H5)3],HRh (CO) [P (C6H5) 3],
oder heterogen, z. B. diese Verbindung auf einem festen Träger, wie Kieselgel, enthalten.or heterogeneous, e.g. B. contain this compound on a solid support such as silica gel.
Die erfindungsgemäße Hydroformylierung erfolgt vorzugsweise bei einer Temperatur von 50 bis 2000C und einem Gesamtdruck von Kohlenmonoxid und Wasserstoff bis zu 200 bar. Man kann das erfindungsgemäße Verfahren in einem organischen Lösungsmittel durchführen, z. B. in einem aliphatischen, cycloaliphatischen oder aromatischen Kohlenwasserstoff.The hydroformylation according to the invention is preferably carried out at a temperature of 50 to 200 ° C. and a total pressure of carbon monoxide and hydrogen of up to 200 bar. The inventive method can be carried out in an organic solvent, e.g. B. in an aliphatic, cycloaliphatic or aromatic hydrocarbon.
Die erfindungsgemäßen Verbindungen können in bekannter Weise in der Parfümerie verwendet werden, z. B. als Aromastoff für parfümierte Produkte in Kombination mi' anderen herkömmlichen HilfsStoffen, z. B. für Seifen, Deodorantien, Reinigungsmittel und Aerosole.The compounds according to the invention can be used in a known manner in perfumery, z. B. as a flavoring for perfumed products in combination with other conventional auxiliaries, e.g. B. for Soaps, deodorants, detergents and aerosols.
Die Beispiele erläutern die Erfindung.The examples illustrate the invention.
Die NMR-Spektren in ppm wurden bei 60 MHz in deuteriertem Chloroform gemessen und mit einem Tetramethylsilan-Standard verglichen.The ppm NMR spectra were measured at 60 MHz in deuterated chloroform and with a tetramethylsilane standard compared.
ftft
Als Katalysator für die Hydroformylierung wird ein heterogener Katalysator verwendet, der durch Umsetzen von Kieselgel mit einem vorgebildeten Komplex vonThe catalyst used for the hydroformylation is a heterogeneous catalyst which is produced by reacting of silica gel with a preformed complex of
(C2H5O)3SiCH2CH2P(C6Hs)2 mit RhHiCOXPfCeHshli(C 2 H 5 O) 3 SiCH 2 CH 2 P (C 6 Hs) 2 with RhHiCOXPfCeHshli
hergestellt wurde und etwa 1,0 Gewichtsprozent Rhodi- to um enthält.and contains about 1.0 percent by weight rhodium.
Als Ausgangsmaterial wird ein Isomerengemisch von ^-Dimethyl-l-il-methylvinyO-cyclopent-S-ol (Plinol) verwendet, das durch thermisches Kracken von Linalool bei 525° C hergestellt wurde.The starting material is an isomer mixture of ^ -Dimethyl-l-il-methylvinyO-cyclopent-S-ol (Plinol) used, which was made by thermal cracking of linalool at 525 ° C.
8,0 g des Plinolgemisches, 2,0 g des Hydroformylierungskatalysators, 5 ml Benzol und 40 ml Cyclohexan werden in einem 100 ml fassenden Autoklaven aus rostfreiem Stahl vermischt. Der Autoklav wird mit einem Gemisch aus gleichen Volumina Wasserstoff und Koh-Ienmonoxid bis zu einem Druck von 80 bar beaufschlagt. Das Gemisch wird bei 1000C 4 Stunden, 30 Minuten gerührt, dann auf Raumtemperatur abgekühlt, filtriert und fraktioniert destilliert Man erhält 5,3 g 3-(2,3-Dimethyl-3-hydroxycyclopentyl)-butanal, Kp. 100 bis 103° C/120 Pa.8.0 g of the Plinol mixture, 2.0 g of the hydroformylation catalyst, 5 ml of benzene and 40 ml of cyclohexane are mixed in a 100 ml stainless steel autoclave. The autoclave is pressurized with a mixture of equal volumes of hydrogen and carbon monoxide up to a pressure of 80 bar. The mixture is stirred at 100 ° C. for 4 hours, 30 minutes, then cooled to room temperature, filtered and fractionally distilled. 5.3 g of 3- (2,3-dimethyl-3-hydroxycyclopentyl) butanal, boiling point 100 to 103 are obtained ° C / 120 Pa.
Das Produkt hat folgendes NMR-Spektrum (ppm):The product has the following NMR spectrum (ppm):
δ = 0,77(Dublett,3H), δ = 0.77 (doublet, 3H),
0,80(Dublett,3H),0.80 (doublet, 3H),
0,97(Dublett,3H),0.97 (doublet, 3H),
l,30(Singulett,3H),1.30 (singlet, 3H),
9,83 (Multiple«, IH).9.83 (Multiple ", IH).
Das Produkt hat einen ausgeprägten Maiglöckchengeruch. The product has a pronounced lily of the valley odor.
Aus den folgenden Bestandteilen wird ein parfümiertes Produkt mit einem Maiglöckchengeruch hergestellt:A perfumed product with a lily of the valley odor is made from the following ingredients:
4545
5050
5555
6060
*) lOprozentige Lösung in Diäthylen-glykolmonoäthyläther.*) 10 percent solution in diethylene glycol monoethyl ether.
Dieses Präparat hat einen zufriedenstellenden Maiglöckchenähnlichen Geruch. Die Geruchseigenschaften werden jedoch durch Zugabe von 200 Gewichtsteilen Plinolaldehyd sehr stark verbessert und abgerundet.This preparation has a satisfactory lily of the valley-like appearance Odor. However, the odor properties are improved by adding 200 parts by weight Plinolaldehyde very much improved and rounded.
C
1* 1IV
C.
1 * 1
Claims (4)
R1 1. Cyclopentane derivatives of the formula II
R 1
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5050576A GB1550004A (en) | 1976-12-03 | 1976-12-03 | Cyclopentane derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2753644A1 DE2753644A1 (en) | 1978-06-08 |
| DE2753644C2 true DE2753644C2 (en) | 1986-09-25 |
Family
ID=10456151
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772753644 Expired DE2753644C2 (en) | 1976-12-03 | 1977-12-01 | Cyclopentane derivatives, process for their preparation and their use |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS6031813B2 (en) |
| CH (1) | CH631148A5 (en) |
| DE (1) | DE2753644C2 (en) |
| FR (1) | FR2372784A1 (en) |
| GB (1) | GB1550004A (en) |
| NL (1) | NL7713270A (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2837480A1 (en) * | 1978-08-28 | 1980-03-20 | Ruhrchemie Ag | METHOD FOR PRODUCING 3- (4-METHYL-3-CYCLOHEXEN-L-YL) BUTYRALDEHYDE |
| JPH0379714U (en) * | 1989-12-08 | 1991-08-14 | ||
| JPH0431000U (en) * | 1990-07-11 | 1992-03-12 | ||
| ES2167829T3 (en) | 1997-11-11 | 2002-05-16 | Firmenich & Cie | NITRILS AND ALDEHIDS DERIVED FROM 3-ISOPROPENYL-1,2-DIMETHYL-1-CYCLOPENTANOL AND ITS USE IN PERFUMERIA. |
| CA3026571A1 (en) | 2016-06-06 | 2017-12-14 | Brain Brew Ventures 3.0 Llc | Method for creating smoked foods and beverages |
-
1976
- 1976-12-03 GB GB5050576A patent/GB1550004A/en not_active Expired
-
1977
- 1977-11-30 FR FR7736105A patent/FR2372784A1/en active Granted
- 1977-12-01 NL NL7713270A patent/NL7713270A/en not_active Application Discontinuation
- 1977-12-01 DE DE19772753644 patent/DE2753644C2/en not_active Expired
- 1977-12-01 JP JP14335877A patent/JPS6031813B2/en not_active Expired
- 1977-12-01 CH CH1472277A patent/CH631148A5/en not_active IP Right Cessation
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT |
Also Published As
| Publication number | Publication date |
|---|---|
| NL7713270A (en) | 1978-06-06 |
| DE2753644A1 (en) | 1978-06-08 |
| GB1550004A (en) | 1979-08-08 |
| JPS5371039A (en) | 1978-06-24 |
| FR2372784B1 (en) | 1981-01-09 |
| JPS6031813B2 (en) | 1985-07-24 |
| CH631148A5 (en) | 1982-07-30 |
| FR2372784A1 (en) | 1978-06-30 |
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