DE1018055B - Process for the production of 7-acetyl-1, 1, 4, 6-tetramethyl-4-ethyl-1, 2, 3, 4-tetrahydronaphthalene with a musky smell - Google Patents
Process for the production of 7-acetyl-1, 1, 4, 6-tetramethyl-4-ethyl-1, 2, 3, 4-tetrahydronaphthalene with a musky smellInfo
- Publication number
- DE1018055B DE1018055B DEG18762A DEG0018762A DE1018055B DE 1018055 B DE1018055 B DE 1018055B DE G18762 A DEG18762 A DE G18762A DE G0018762 A DEG0018762 A DE G0018762A DE 1018055 B DE1018055 B DE 1018055B
- Authority
- DE
- Germany
- Prior art keywords
- ethyl
- tetramethyl
- tetrahydronaphthalene
- acetyl
- known per
- 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
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- XTWHZKTXSJZYLK-UHFFFAOYSA-N 1-(5-ethyl-3,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)ethanone Chemical compound CC(=O)C1=C(C)C=C2C(CC)(C)CCC(C)(C)C2=C1 XTWHZKTXSJZYLK-UHFFFAOYSA-N 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- HMJHOYFMNZAJFP-UHFFFAOYSA-N 4-ethyl-1,1,4,6-tetramethyl-2,3-dihydronaphthalene Chemical compound C1=C(C)C=C2C(CC)(C)CCC(C)(C)C2=C1 HMJHOYFMNZAJFP-UHFFFAOYSA-N 0.000 claims description 4
- KCOMWVWZVIVQFP-UHFFFAOYSA-N 5-methyl-5-(4-methylphenyl)hexan-2-one Chemical compound CC(CCC(C)=O)(C)C1=CC=C(C=C1)C KCOMWVWZVIVQFP-UHFFFAOYSA-N 0.000 claims description 4
- VBCIOOKAKHGVMI-UHFFFAOYSA-N 5-methylhex-5-en-2-one Chemical compound CC(=C)CCC(C)=O VBCIOOKAKHGVMI-UHFFFAOYSA-N 0.000 claims description 4
- QHPWUKFONYNREE-UHFFFAOYSA-N 3,6-dimethyl-6-(4-methylphenyl)heptan-3-ol Chemical compound CC(CC)(CCC(C)(C1=CC=C(C=C1)C)C)O QHPWUKFONYNREE-UHFFFAOYSA-N 0.000 claims description 3
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 claims description 3
- 244000309464 bull Species 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000003205 fragrance Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
- 241000402754 Erythranthe moschata Species 0.000 description 3
- 230000021736 acetylation Effects 0.000 description 3
- 238000006640 acetylation reaction Methods 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- FKUPPRZPSYCDRS-UHFFFAOYSA-N Cyclopentadecanolide Chemical compound O=C1CCCCCCCCCCCCCCO1 FKUPPRZPSYCDRS-UHFFFAOYSA-N 0.000 description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
- 239000012346 acetyl chloride Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- OSOIQJGOYGSIMF-UHFFFAOYSA-N cyclopentadecanone Chemical compound O=C1CCCCCCCCCCCCCC1 OSOIQJGOYGSIMF-UHFFFAOYSA-N 0.000 description 2
- 150000002468 indanes Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- -1 musk xylene Chemical class 0.000 description 2
- XMWRWTSZNLOZFN-UHFFFAOYSA-N musk xylene Chemical group CC1=C(N(=O)=O)C(C)=C(N(=O)=O)C(C(C)(C)C)=C1N(=O)=O XMWRWTSZNLOZFN-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- RNDVGJZUHCKENF-UHFFFAOYSA-N 5-hexen-2-one Chemical compound CC(=O)CCC=C RNDVGJZUHCKENF-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical class C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-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
- C11B9/0042—Essential oils; Perfumes compounds containing condensed hydrocarbon rings
- C11B9/0046—Essential oils; Perfumes compounds containing condensed hydrocarbon rings containing only two condensed rings
- C11B9/0049—Essential oils; Perfumes compounds containing condensed hydrocarbon rings containing only two condensed rings the condensed rings sharing two common C atoms
- C11B9/0053—Essential oils; Perfumes compounds containing condensed hydrocarbon rings containing only two condensed rings the condensed rings sharing two common C atoms both rings being six-membered
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)
- Fats And Perfumes (AREA)
- Cosmetics (AREA)
Description
Verfahren zur Herstellung von moschusartig riechendem 7-Acetyl-1, 1, 4, 6-tetramethyl-4-äthyl-1, 2, 3, 4-tetrahydronaphthalin Die Erfindung bezieht sich auf die Herstellung eines neuen Moschusriechstoffes, nämlich auf die Herstellung des 7-Acetyl-1, 1, 4, 6-tetramethyl-4-äthyl-1, 2, 3, 4-tetrahydronaphthalins.Process for the production of musky smelling 7-acetyl-1, 1, 4, 6-tetramethyl-4-ethyl-1, 2, 3, 4-tetrahydronaphthalene The invention relates on the production of a new musk fragrance, namely on the production of 7-acetyl-1, 1, 4, 6-tetramethyl-4-ethyl-1, 2, 3, 4-tetrahydronaphthalene.
Die meisten bekannten moschusartig riechenden Verbindungen fallen unter zwei Gruppen von Stoffen: 1. Nitrierte aromatische Verbindungen, wie Moschusxylol, das ist 2, 4, 6-Trinitro-1, 3-dimethyl-5-tertiäres-butylbenzol, 2. makrocyclische Ketone, Laktone oder Ester, wie Cvclopentadecanon, Cyclopentadecanolid und Äthylenbrassvlat.Most known musky-smelling compounds are dropped under two groups of substances: 1. Nitrated aromatic compounds, such as musk xylene, that is 2, 4, 6-trinitro-1, 3-dimethyl-5-tertiary-butylbenzene, 2nd macrocyclic Ketones, lactones or esters, such as cyclopentadecanone, cyclopentadecanolide and ethylene brassolate.
Wenngleich die Glieder in der ersten Gruppe billig herzustellen sind, leiden sie an dem Nachteil, daß sie nicht licht- und alkalibeständig sind, wodurch sie z. B. in Seife häufig eine Verfärbung verursachen. Glieder der zweiten Gruppe sind, wenngleich sie gegen Licht und Alkali ausreichend beständig sind, schwierig herzustellen und verhältnismäßig teuer.Although the links in the first group are cheap to manufacture, they suffer from the disadvantage that they are not lightfast and alkali-resistant, whereby she z. B. in soap often cause discoloration. Members of the second group are difficult, although they are sufficiently resistant to light and alkali to manufacture and relatively expensive.
Es ist auch ein Verfahren zur Herstellung von moschusartigen Riechstoffen bekanntgeworden, das die Herstellung von substituierten Tetrahydronaphthalinen betrifft. Dieses Verfahren führt aber zu Zwischenprodukten, die größere Mengen von Verunreinigungen enthalten, die bei der Acetylierung Stoffe ergeben, die keinen oder sogar einen unerwünschten Geruch haben und daher den Geruch des fertigen Erzeugnisses beeinträchtigen. Tatsächlich weisen bei weitem nicht alle Acetylierungsprodukte von Indanen oder substituierten Indanen einen typischen Moschusgeruch auf.It is also a method of making musky fragrances became known, which relates to the production of substituted tetrahydronaphthalenes. However, this process leads to intermediates that contain larger amounts of impurities contain substances which, when acetylated, produce substances that do not contain any or even one have an undesirable odor and therefore affect the odor of the finished product. In fact, by far not all acetylation products of indanes or substituted indanes have a typical musky odor.
Es wurde nun gefunden, daß man eine neue chemische Verbindung herstellen kann, welche eine moschusähnliche Geruchsnote aufweist, gegen Licht und Alkalien äußerst beständig, gleichzeitig aber billig und mit gleichmäßiger Riechstoffqualität herzustellen ist ohne Beeinträchtigung des Geruches durch unerwünschte Nebenprodukte. Die neue Moschusv erbindung wird durch Umsetzung von Toluol mit Methallylaceton in Gegenwart eines Katalysators, wie Aluminiumchlorid, Umsetzung des erhaltenen 5-Methyl-5-p-tolyl-2-hexanons mit Äthylmagnesiumbromid zu 3, 6-Dimethyl-6-p-tolyl-3-heptanol, Cyclisierung dieser Verbindung zu 1, 1, 4, 6-Tetramethyl-4-äthyl-1, 2, 3, 4-tetrahydronaphthalin in Gegenwart eines Cyclisierungsmittels, wie Schwefelsäure, und schließlich Acetylierung der anfallenden Verbindung, z. B. mit Acetylchlorid, in Gegenwart von wasserfreiem Aluminiumchlorid hergestellt.It has now been found that a new chemical compound can be produced can, which has a musky odor note, against light and alkalis extremely stable, but at the same time cheap and with a uniform fragrance quality can be produced without the odor being impaired by undesired by-products. The new musk compound is made by reacting toluene with methallylacetone in the presence of a catalyst such as aluminum chloride, reaction of the obtained 5-methyl-5-p-tolyl-2-hexanones with ethylmagnesium bromide to 3, 6-dimethyl-6-p-tolyl-3-heptanol, Cyclization of this compound to 1, 1, 4, 6-tetramethyl-4-ethyl-1, 2, 3, 4-tetrahydronaphthalene in the presence of a cyclizing agent such as sulfuric acid, and finally acetylation the resulting connection, e.g. B. with acetyl chloride, in the presence of anhydrous Aluminum chloride produced.
Die einzelnen Verfahrensschritte sind an sich belcannt. So wurden die ersten drei Stufen beispielsweise bereits mit Allylaceton durchgeführt (vgl. z. B. Comptes rendus hebd., Bd. 226, 1948, S. 673 bis 675; Bull. Soc. Chim. France, 1949, S. 855 bis 857, und J. Am. Chem. Soc., Bd.62, 1940, S.3405 bis 3410). Auch die Acetylierung erfolgt in an sich bekannter Weise. Man erhält jedoch unter Verwendung von Methallylaceton als Ausgangsstoff als Endprodukt einen Moschusriechstoff, der noch wesentlich alkali-und lichtbeständiger als die bisher bekannten Produkte ist.The individual process steps are scanned per se. So were the first three stages, for example, have already been carried out with allylacetone (cf. z. B. Comptes rendus hebd., Vol. 226, 1948, pp. 673-675; Bull. Soc. Chim. France, 1949, pp. 855-857, and J. Am. Chem. Soc., Vol. 62, 1940, pp. 3405 to 3410). Even the acetylation takes place in a manner known per se. However, using of methallylacetone as the starting material as the end product a musk fragrance, the is still considerably more resistant to alkali and light than the previously known products.
Es ist leicht ersichtlich, daß die neue moschusähnlich riechende Verbindung in den verschiedenartigsten Zubereitungen verwendet werden kann, z. B. in Parfüms, Kosmetika und Seifen.It can be easily seen that the new musk-like smelling compound can be used in a wide variety of preparations, e.g. B. in perfumes, Cosmetics and soaps.
Das folgende Beispiel erläutert die Durchführung der Erfindung.The following example illustrates the practice of the invention.
Beispiel a) In ein 5° kaltes Gemisch aus 450 g Toluol und 200 g gepulvertem wasserfreiem Aluminiumchlorid werden unter gutem Rühren und Kühlen (5 bis 10°) im Verlauf von 3/4 Stunden 112 g Methallylaceton gegeben. Das Gemisch wird weitere 3 Stunden bei 10° gerührt und mit 1200 g Eisstückchen abgeschreckt. Das Öl wird abgetrennt und nacheinander mit 5o/oiger Salzsäure, 5°/oiger Natronlauge und Wasser gewaschen. Nach dem Abdestillieren des überschüssigen Toluols wird das Produkt im Vakuum destilliert. Es werden 141,5 g, Kp.4,5 = 118 bis 130°, als farbloses Öl erhalten. Durch erneute fraktionierte Destillation erhält man reines 5-Methyl-5-p-tolyl-2-hexanon, Kp.2 = 108°, nD = 1,5112.Example a) In a mixture of 450 g of toluene and 200 g of powdered anhydrous aluminum chloride at 5 ° C., 112 g of methallylacetone are added with thorough stirring and cooling (5 to 10 °) in the course of 3/4 hours. The mixture is stirred for a further 3 hours at 10 ° and quenched with 1200 g of ice chips. The oil is separated off and washed successively with 5% hydrochloric acid, 5% sodium hydroxide solution and water. After the excess toluene has been distilled off, the product is distilled in vacuo. 141.5 g, boiling point 4.5 = 118 to 130 °, are obtained as a colorless oil . Another fractional distillation gives pure 5-methyl-5-p-tolyl-2-hexanone, b.p. 2 = 108 °, nD = 1.5112.
b) 204 g 5-Methyl-5-p-tolyl-2-hexanon werden bei 34° mit einer Ätherlösung von Äthylmagnesiumbromid umgesetzt, die durch Einwirkung von 120 g Äthylbromid in 350 g Diäthyläther auf 26,5 g Magnesiumspäne erhalten wurde. Nach lstündigem.Erhitzen unter Rückfluß wird die Lösung in einem Gemisch aus 300 g Eisstückchen und 300 g Wasser abgeschreckt. Nach Neutralisation der Komplexverhindung mit 402 g .10"/oiger .Salzsäure wird die Ätherlösung mit Wasser und verdünnter Natriumcarbonatlösung gewaschen. Der Äther wird entfernt und das zurückbleibende Öl im Vakuum destilliert. Das 3, 6-Dimethyl-6-tolyl-3-heptanol wird als farblose viskose Flüssigkeit erhalten, Kp.1,5 = 121 bis 122°, nD = 1,5053 bis 1,5063. Die Ausbeute beträgt 132 g = 56,3 0/a der Theorie.b) 204 g of 5-methyl-5-p-tolyl-2-hexanone are reacted at 34 ° with an ethereal solution of ethylmagnesium bromide, which was obtained by the action of 120 g of ethyl bromide in 350 g of diethyl ether on 26.5 g of magnesium shavings. After refluxing for 1 hour, the solution is quenched in a mixture of 300 g of ice pieces and 300 g of water. After neutralization of the complex compound with 402 g of 10% hydrochloric acid, the ether solution is washed with water and dilute sodium carbonate solution. The ether is removed and the remaining oil is distilled in vacuo. The 3,6-dimethyl-6-tolyl-3-heptanol is obtained as a colorless viscous liquid, bp 1.5 = 121 to 122 °, nD = 1.5053 to 1.5063, the yield is 132 g = 56.3% of theory.
c) 117 ccm 93%ige Schwefelsäure werden auf 0° abgekühlt und 117 g des oben beschriebenen 3, 6-Dimethyl-6-p-tolyl-3-heptanols unter Rühren im Verlauf von 45 Minuten zugegeben, wobei man die Temperatur auf 0° hält. Das Rühren wird eine weitere Stunde fortgesetzt. Die Lösung wird dann mit Eis abgeschreckt. Das C51 wird in Benzol aufgenommen, mit Wasser, 5%iger Natronlauge und wieder mit Wasser gewaschen, bis es neutral ist. Das Benzol wird abdestilliert und das Öl im Vakuum über 2 g Natriumcarbonat destilliert. Es werden 94,5 g 1, 1, 4, 6-Tetramethyl-4-äthyl-1, 2, 3, 4-tetrahydronaphthalin als farbloses Öl erhalten, KP., = 99 bis 100°, n" = 1,5200.c) 117 cc of 93% sulfuric acid are cooled to 0 ° and 117 g of the above-described 3, 6-dimethyl-6-p-tolyl-3-heptanol with stirring in the course added of 45 minutes, the temperature being kept at 0 °. The stirring will continued for another hour. The solution is then quenched with ice. That C51 is taken up in benzene, with water, 5% sodium hydroxide solution and again with water washed until it is neutral. The benzene is distilled off and the oil in vacuo distilled over 2 g of sodium carbonate. There are 94.5 g of 1, 1, 4, 6-tetramethyl-4-ethyl-1, 2, 3, 4-tetrahydronaphthalene obtained as a colorless oil, KP., = 99 to 100 °, n "= 1.5200.
d) Ein Gemisch aus 22,5 g Acetylchlorid und 54 g des oben beschriebenen 1, 1, 4, 6-Tetramethyl-4-äthyl-1, 2, 3, 4-tetrahydronaphthalins wird im Verlauf von 1 Stunde zu einer Suspension von 38,5 g wasserfreiem Aluminiumchlorid in 135 g Äthylendichlorid unter ständigem Rühren und Kühlen gegeben, um die Reaktionstemperatur bei 20 bis 25° zu halten. Nach der Zugabe wird das Rühren 30 Minuten bei 40° fortgesetzt. Die Lösung wird auf Eis abgeschreckt, die Äthylenchloridlösung abgetrennt und mit Wasser neutral gewaschen. Das Äthylendichlorid wurde abdestilliert, und das im Vakuum destillierte zurückbleibende C51 ergab 52 g 7-Acetyl-1, 1, 4, 6-tetramethyl-4-äthyl-1, 2, 3, 4-tetrahydronaphthalin, Kp.l = 129 bis 130,5°, nD = 1,5390. Die Verbindung ist eine viskose, farblose Flüssigkeit mit angenehmem moschusartigem Geruch. Analyse für C18 H26 O Berechnet . .. . . . . . . ....... C 83,70%, H 10,07%; gefunden . .. . . .. .. . . . . .. . C 83,80%, H 10,090/a.d) A mixture of 22.5 g of acetyl chloride and 54 g of the above 1, 1, 4, 6-tetramethyl-4-ethyl-1, 2, 3, 4-tetrahydronaphthalene is used in the course of 1 hour to a suspension of 38.5 g of anhydrous aluminum chloride in 135 g ethylene dichloride added with constant stirring and cooling to the reaction temperature hold at 20 to 25 °. After the addition, stirring is continued at 40 ° for 30 minutes. The solution is quenched on ice, the ethylene chloride solution is separated and with Washed neutral in water. The ethylene dichloride was distilled off, and that in vacuo distilled remaining C51 gave 52 g of 7-acetyl-1, 1, 4, 6-tetramethyl-4-ethyl-1, 2,3,4-tetrahydronaphthalene, boiling point = 129 to 130.5 °, nD = 1.5390. The connection is a viscous, colorless liquid with a pleasant musky odor. analysis Calculated for C18 H26 O. ... . . . . . ....... C 83.70%, H 10.07%; found . ... . .. ... . . . ... C 83.80%, H 10.090 / a.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US1018055XA | 1955-02-23 | 1955-02-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1018055B true DE1018055B (en) | 1957-10-24 |
Family
ID=22286500
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEG18762A Pending DE1018055B (en) | 1955-02-23 | 1956-01-10 | Process for the production of 7-acetyl-1, 1, 4, 6-tetramethyl-4-ethyl-1, 2, 3, 4-tetrahydronaphthalene with a musky smell |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1018055B (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL74524C (en) * | ||||
| DE918747C (en) * | 1951-08-27 | 1954-10-04 | P F W Of America Inc | Process for the production of artificial musk fragrances from m- and p-cymene |
-
1956
- 1956-01-10 DE DEG18762A patent/DE1018055B/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL74524C (en) * | ||||
| DE918747C (en) * | 1951-08-27 | 1954-10-04 | P F W Of America Inc | Process for the production of artificial musk fragrances from m- and p-cymene |
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