DE1192771B - Fragrances and fragrance compositions - Google Patents
Fragrances and fragrance compositionsInfo
- Publication number
- DE1192771B DE1192771B DEV25022A DEV0025022A DE1192771B DE 1192771 B DE1192771 B DE 1192771B DE V25022 A DEV25022 A DE V25022A DE V0025022 A DEV0025022 A DE V0025022A DE 1192771 B DE1192771 B DE 1192771B
- Authority
- DE
- Germany
- Prior art keywords
- fragrances
- iii
- weight
- parts
- aldehyde
- 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
- 239000000203 mixture Substances 0.000 title claims description 14
- 239000003205 fragrance Substances 0.000 title claims description 12
- 238000005984 hydrogenation reaction Methods 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 4
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 3
- 229930195729 fatty acid Natural products 0.000 claims description 3
- 239000000194 fatty acid Substances 0.000 claims description 3
- 150000004665 fatty acids Chemical class 0.000 claims description 3
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 150000001299 aldehydes Chemical class 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- CSUCBYYLYMFEFB-BJMVGYQFSA-N (2e)-2-(3,3-dimethyl-2-bicyclo[2.2.1]heptanylidene)acetaldehyde Chemical compound C1CC2\C(=C/C=O)C(C)(C)C1C2 CSUCBYYLYMFEFB-BJMVGYQFSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- CRPUJAZIXJMDBK-UHFFFAOYSA-N camphene Chemical compound C1CC2C(=C)C(C)(C)C1C2 CRPUJAZIXJMDBK-UHFFFAOYSA-N 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- PXRCIOIWVGAZEP-UHFFFAOYSA-N Primaeres Camphenhydrat Natural products C1CC2C(O)(C)C(C)(C)C1C2 PXRCIOIWVGAZEP-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- XCPQUQHBVVXMRQ-UHFFFAOYSA-N alpha-Fenchene Natural products C1CC2C(=C)CC1C2(C)C XCPQUQHBVVXMRQ-UHFFFAOYSA-N 0.000 description 2
- 229930006739 camphene Natural products 0.000 description 2
- ZYPYEBYNXWUCEA-UHFFFAOYSA-N camphenilone Natural products C1CC2C(=O)C(C)(C)C1C2 ZYPYEBYNXWUCEA-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 238000003756 stirring 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
- WRPYDXWBHXAKPT-UHFFFAOYSA-N (2-ethenylphenyl) acetate Chemical compound CC(=O)OC1=CC=CC=C1C=C WRPYDXWBHXAKPT-UHFFFAOYSA-N 0.000 description 1
- OFHHDSQXFXLTKC-UHFFFAOYSA-N 10-undecenal Chemical compound C=CCCCCCCCCC=O OFHHDSQXFXLTKC-UHFFFAOYSA-N 0.000 description 1
- GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical compound C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 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
- 240000000513 Santalum album Species 0.000 description 1
- 235000008632 Santalum album Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000001926 citrus aurantium l. subsp. bergamia wright et arn. oil Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- WPFVBOQKRVRMJB-UHFFFAOYSA-N hydroxycitronellal Chemical compound O=CCC(C)CCCC(C)(C)O WPFVBOQKRVRMJB-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000008379 phenol ethers Chemical class 0.000 description 1
- 239000001738 pogostemon cablin oil Substances 0.000 description 1
- 150000007659 semicarbazones Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000126 substance Substances 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
- C11B9/0042—Essential oils; Perfumes compounds containing condensed hydrocarbon rings
- C11B9/0046—Essential oils; Perfumes compounds containing condensed hydrocarbon rings containing only two condensed rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/13—Monohydroxylic alcohols containing saturated rings
- C07C31/137—Monohydroxylic alcohols containing saturated rings polycyclic with condensed ring systems
-
- 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
- C07C45/68—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 by increase in the number of carbon atoms
- C07C45/72—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 by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
- C07C45/74—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 by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
- C07C47/225—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing rings other than six-membered aromatic 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)
- Fats And Perfumes (AREA)
Description
Riechstoffe und Riechstoffkompositionen Die Erfindung betrifft Riechstoffe und Riechstoff kompositionen, welche 3-(Camphenyl-8)-2-methylpropen-3-al-1 (I) und seine Hydrierungsprodukte, 3 - (Camphenyl - 8) - 2 - methyl -1- hydroxypropan (II) und 3-(Isocamphanyl-8)-2-methyl-l-hydroxypropan (III) sowie deren Mischungen und Ester enthalten. Gegenüber geruchlich ähnlichen Riechstoffen auf Camphenbasis, wie z. B. den bekannten perhydrierten Additionsprodukten von Camphen und Phenoläthern, haben die hier beschriebenen Produkte - abgesehen von ihren neuartigen, die Riechstoffpalette bereichernden Geruchsnoten - den Vorteil der technisch einfacheren Herstellbarkeit und der absoluten Seifenechtheit der Alkohole (II) und (III). Es wurde gefunden, daß der bei der Kondensation des 8-Formylcamphens mit Propionaldehyd in Gegenwart von stark basischen Katalysatoren, beispielsweise Natriumalkoholaten, entstehende a-,(3-, y-,ä-ungesättigte Aldehyd (I) sowie seine Hydrierungsprodukte (II) und (III) und deren Ester mit niederen Fettsäuren ausgezeichnete Riechstoffe darstellen.Fragrances and fragrance compositions The invention relates to fragrances and fragrance compositions which 3- (camphenyl-8) -2-methylpropen-3-al-1 (I) and its hydrogenation products, 3 - (camphenyl-8) -2-methyl -1- hydroxypropane (II) and 3- (isocamphanyl-8) -2-methyl-1-hydroxypropane (III) and mixtures and esters thereof. Compared to odor-similar odorous substances based on camphene, such as. B. the well-known perhydrogenated addition products of camphene and phenol ethers, the products described here - apart from their novel odor notes enriching the range of fragrances - have the advantage that alcohols (II) and (III) are technically easier to manufacture and that they are absolutely soap-fast. It has been found that the α-, (3-, γ-, γ-unsaturated aldehyde (I) and its hydrogenation products (II) and formed during the condensation of 8-formylcamphene with propionaldehyde in the presence of strongly basic catalysts, for example sodium alcoholates (III) and their esters with lower fatty acids are excellent fragrances.
Der Aldehyd (1) hat einen starken holzig-grünen und haftenden Geruch und ist als solcher in Kompositionen gut verwendbar.The aldehyde (1) has a strong woody-green and sticky odor and as such is well usable in compositions.
Der bei vollständiger Hydrierung des I, z. B. mit Raney-Nickel als Katalysator und 50 at Wasserstoff bei Temperaturen von etwa 90 bis 100°C, in guter Ausbeute erhaltene Alkohol (III) besitzt einen feinen Duft nach Zedern und Sandelholz. Man kann die Hydrierung jedoch auch so leiten, daß im Endprodukt der Aldehyd (I) und die Alkohole (II) und (III) vorliegen, beispielsweise durch Unterbrechen der Hydrierung nach Aldehydbestimmung. Dabei hat sich gezeigt, daß auf diese Weise erhaltene Mischungen, die z. B. 3 bis 5% Aldehyd (1), 50 bis 60% Alkohol (II) und 30 bis 40% Alkohol (III) enthalten, außerordentlich gut verwendbar sind, da sie die holzig-grüne Note des Aldehyds (I) mit der milden holzigen Note der Alkohole (II) und (III) vereinen.When the I is fully hydrogenated, e.g. B. with Raney nickel as Catalyst and 50 atm of hydrogen at temperatures of about 90 to 100 ° C, in good Alcohol (III) obtained in the yield has a fine scent of cedar and sandalwood. However, the hydrogenation can also be conducted in such a way that the aldehyde (I) in the end product and the alcohols (II) and (III) are present, for example by interrupting the Hydrogenation according to aldehyde determination. It has been shown that obtained in this way Mixtures z. B. 3 to 5% aldehyde (1), 50 to 60% alcohol (II) and 30 to 40% Alcohol (III) contain, are extremely useful, since they are the woody-green Combine the note of the aldehyde (I) with the mild woody note of the alcohols (II) and (III).
Auch kann die Hydrierung so geleitet werden, daß das Produkt aldehydfrei anfällt und nur die Alkohole (II) und (III) enthält. Dieses Gemisch zeichnet sich besonders durch die Haltbarkeit der Verbindungen und des Geruchs in Seifen aus.The hydrogenation can also be conducted in such a way that the product is free from aldehyde is obtained and only contains the alcohols (II) and (III). This mixture stands out especially by the durability of the compounds and the smell in soaps.
Je nach gewünschtem Verwendungszweck ist es also möglich, durch einfache katalytische Hydrierung wertvolle seifenechte Riechstoffe aus dem Aldehyd (I) herzustellen. Die durch Umsetzung der Alkohole mit niederen Fettsäuren erhältlichen Ester, z. B. 3-(Isocamphanyl-8)-2-methyl-l-acetoxypropan, zeichnen sich ebenfalls durch einen angenehmen Holzgeruch aus und lassen sich gut als Komponenten von Riechstoffmischungen verwenden. Beispiel 1 Kondensation von 8-Formylcamphen mit Propionaldehyd In einem 6-1-Sulfierkolben mit Rührer, Tropftrichter und Thermometer werden 250 g 10%ige Natriummethylatlösung und 100 ml Methanol vorgelegt und auf + 10°C abgekühlt. Bei dieser Temperatur läßt man eine Mischung aus 640 g 8-Formylcamphen, 320 g Propionaldehyd und 500 m1Methanol unter Rühren schnell zulaufen. Die Temperatur wird dabei zwischen 10 und 20°C gehalten. Die Zulaufzeit soll etwa 10 bis 15 Minuten betragen. Dann wird unter Rühren 3 Stunden auf 20 bis 25°C gehalten, mit Essigsäure neutralisiert und über Nacht stehengelassen. Am nächsten Tag wird mit Wasser verdünnt, bis sich das 0l gut abscheidet. Das Öl wird im Scheidetrichter abgetrennt und die wäßrige Schicht einmal mit Benzol extrahiert. Die Ölschicht und die Benzollösung werden vereinigt, mit Wassergewaschen, mit Natriumsulfat getrocknet, vom Benzol befreit und der Rückstand im Vakuum destilliert. Man erhält 420 g (I) als gelbliche stark viskose Flüssigkeit vom Kp.o,o5 bis o,oa 92 bis 99°C (nö° = 1,5665 bis 1,5670) und gewinnt etwa 270 bis 290 g 8-Formylcamphen zurück, das nochmals zur Reaktion gebracht werden kann.Depending on the intended use, it is therefore possible to produce valuable, soap-resistant fragrances from the aldehyde (I) by simple catalytic hydrogenation. The esters obtainable by reacting the alcohols with lower fatty acids, e.g. B. 3- (Isocamphanyl-8) -2-methyl-l-acetoxypropane, are also characterized by a pleasant wood odor and can be used well as components of odoriferous mixtures. Example 1 Condensation of 8-formylcamphene with propionaldehyde 250 g of 10% sodium methylate solution and 100 ml of methanol are placed in a 6-1 sulphonation flask equipped with a stirrer, dropping funnel and thermometer and the mixture is cooled to + 10.degree. At this temperature, a mixture of 640 g of 8-formylcamphene, 320 g of propionaldehyde and 500 ml of methanol is allowed to run in rapidly with stirring. The temperature is kept between 10 and 20 ° C. The feed time should be about 10 to 15 minutes. The mixture is then kept at 20 to 25 ° C. for 3 hours with stirring, neutralized with acetic acid and left to stand overnight. The next day, it is diluted with water until the oil separates out well. The oil is separated off in a separatory funnel and the aqueous layer is extracted once with benzene. The oil layer and the benzene solution are combined, washed with water, dried with sodium sulfate, freed from benzene, and the residue is distilled in vacuo. 420 g of (I) are obtained as a yellowish, highly viscous liquid with a boiling point of 0.05 to 0.02 ° C. to 99 ° C. (nö ° = 1.5665 to 1.5670) and about 270 to 290 g of 8-formylcamphene are recovered that can be reacted again.
Semicarbazon, F. 207 bis 209°C (aus Äthanol). 2,4-Dinitrophenylhydrazon, F. 228 bis 229°C (aus Athylacetat). Beispiel 2 Hydrierung des 3-(Camphenyl-8)-2-methylpropen-3-als-1 (I) 800g (1) werden in 420m1 960%igem Äthanol gelöst und mit 80g Raney-Nickel bei 80 bis 90°C und 50 at Wasserstoff hydriert, bis keine Wasserstoffaufnahme mehr erfolgt. Insgesamt werden etwa 120l Wasserstoff aufgenommen. Das Reaktionsprodukt wird vom Katalysator und Äthanol befreit und fraktioniert destilliert. Man erhält etwa 60 g Vorlauf und etwa 650 g reines 3-(Isocamphanyl-8)-2-methyl-l-hydroxypropan (III) als farblose, viskose Flüssigkeit mit angenehm mildem Holzgeruch; Kp.o,2 bis o,a 107 bis 112°C (nö = 1,4925 bis 1,4928).Semicarbazone, m.p. 207-209 ° C (from ethanol). 2,4-dinitrophenylhydrazone, Mp 228-229 ° C (from ethyl acetate). Example 2 Hydrogenation of 3- (camphenyl-8) -2-methylpropene-3-than-1 (I) 800g (1) are dissolved in 420m1 960% ethanol and mixed with 80g Raney nickel 80 to 90 ° C and 50 atm hydrogen hydrogenated until there is no more hydrogen uptake. A total of around 120 liters of hydrogen are absorbed. The reaction product is from Catalyst and ethanol freed and fractionally distilled. You get about 60 g first run and about 650 g pure 3- (isocamphanyl-8) -2-methyl-l-hydroxypropane (III) as a colorless, viscous liquid with a pleasantly mild wood odor; Kp.o, 2 to o, a 107 to 112 ° C (nö = 1.4925 to 1.4928).
Der Vorlauf entfärbt KMn04-Lösung und zeigt damit den ungesättigten Charakter seiner Inhaltsstoffe (I) und (II) an. Beispiel 3 3-(Isocamphanyl-8)-2-methyl-l-acetoxypropan 125 g 3-(Isocamphanyl-8)-2-methyl-1-hydroxypropan (III), nö = 1,4928, werden mit 125 g frisch destilliertem Essigsäureanhydrid und 125 g getrocknetem Pyridin 3 Stunden am Rückfluß gekocht. Dann wird abgekühlt und bei 20°C mit 200 ml Wasser verdünnt. Die Mischung wird in einem Scheidetrichter viermal mit verdünnter Salzsäure zur Entfernung des Pyridins gewaschen, dann wird mit Wasser neutral gewaschen. Das Öl wird zur geruchlichen Reinigung nochmals mit Wasserdampf ausgeblasen. Nach dem Trocknen mit Natriumsulfat wird im Vakuum fraktioniert destilliert.The first run decolorizes KMn04 solution and shows the unsaturated one Character of its ingredients (I) and (II). Example 3 3- (Isocamphanyl-8) -2-methyl-1-acetoxypropane 125 g of 3- (isocamphanyl-8) -2-methyl-1-hydroxypropane (III), not = 1.4928, are mixed with 125 g of freshly distilled acetic anhydride and 125 g of dried pyridine for 3 hours refluxed. It is then cooled and diluted at 20 ° C. with 200 ml of water. The mixture is added four times with dilute hydrochloric acid in a separatory funnel Washed removal of the pyridine, then washed neutral with water. The oil is blown out again with steam to clean the odor. After drying fractional distillation is carried out in vacuo with sodium sulfate.
Kp.o,2 92 bis 98°C (n1 = 1,4792).
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEV25022A DE1192771B (en) | 1963-08-14 | 1963-12-12 | Fragrances and fragrance compositions |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DD10016563 | 1963-08-14 | ||
| DEV25022A DE1192771B (en) | 1963-08-14 | 1963-12-12 | Fragrances and fragrance compositions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1192771B true DE1192771B (en) | 1965-05-13 |
Family
ID=25747039
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEV25022A Pending DE1192771B (en) | 1963-08-14 | 1963-12-12 | Fragrances and fragrance compositions |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1192771B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1993002998A1 (en) * | 1991-07-26 | 1993-02-18 | Henkel Kommanditgesellschaft Auf Aktien | Bicyclic compounds, their preparation and their use |
-
1963
- 1963-12-12 DE DEV25022A patent/DE1192771B/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1993002998A1 (en) * | 1991-07-26 | 1993-02-18 | Henkel Kommanditgesellschaft Auf Aktien | Bicyclic compounds, their preparation and their use |
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