DE1017162B - Process for the preparation of low molecular weight 1-alkyl-6-acetyl-1,4,7-trimethyl-1,2,4-tetrahydronaphthalenes with a musk-like odor - Google Patents
Process for the preparation of low molecular weight 1-alkyl-6-acetyl-1,4,7-trimethyl-1,2,4-tetrahydronaphthalenes with a musk-like odorInfo
- Publication number
- DE1017162B DE1017162B DEG18760A DEG0018760A DE1017162B DE 1017162 B DE1017162 B DE 1017162B DE G18760 A DEG18760 A DE G18760A DE G0018760 A DEG0018760 A DE G0018760A DE 1017162 B DE1017162 B DE 1017162B
- Authority
- DE
- Germany
- Prior art keywords
- trimethyl
- acetyl
- tetrahydronaphthalenes
- alkyl
- molecular weight
- 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
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title description 2
- 238000004519 manufacturing process Methods 0.000 claims description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- ZIDUJCHAYXSXNA-UHFFFAOYSA-N 5-(4-methylphenyl)hexan-2-one Chemical compound CC(=O)CCC(C)C1=CC=C(C)C=C1 ZIDUJCHAYXSXNA-UHFFFAOYSA-N 0.000 claims 1
- CDKFWIMBZAUBRS-UHFFFAOYSA-M [I-].CC[Mg+] Chemical compound [I-].CC[Mg+] CDKFWIMBZAUBRS-UHFFFAOYSA-M 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- 238000009833 condensation Methods 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 238000007363 ring formation reaction Methods 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-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
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 239000012230 colorless oil Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- -1 xylene musk Chemical class 0.000 description 3
- IVCNLZBNXHUKOZ-UHFFFAOYSA-N 1-(3,5,5,8-tetramethyl-7,8-dihydro-6h-naphthalen-2-yl)ethanone Chemical compound CC1=C(C(C)=O)C=C2C(C)CCC(C)(C)C2=C1 IVCNLZBNXHUKOZ-UHFFFAOYSA-N 0.000 description 2
- FKUPPRZPSYCDRS-UHFFFAOYSA-N Cyclopentadecanolide Chemical compound O=C1CCCCCCCCCCCCCCO1 FKUPPRZPSYCDRS-UHFFFAOYSA-N 0.000 description 2
- 241000402754 Erythranthe moschata Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- 238000001816 cooling Methods 0.000 description 2
- OSOIQJGOYGSIMF-UHFFFAOYSA-N cyclopentadecanone Chemical compound O=C1CCCCCCCCCCCCCC1 OSOIQJGOYGSIMF-UHFFFAOYSA-N 0.000 description 2
- XMWRWTSZNLOZFN-UHFFFAOYSA-N musk xylene Chemical compound 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
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- GZQXIYBMXGYNFG-UHFFFAOYSA-N 1,4,4,6-tetramethyl-2,3-dihydro-1h-naphthalene Chemical compound CC1=CC=C2C(C)CCC(C)(C)C2=C1 GZQXIYBMXGYNFG-UHFFFAOYSA-N 0.000 description 1
- SSTYKTNTECTUHB-UHFFFAOYSA-N 1-(5-ethyl-3,5,8-trimethyl-7,8-dihydro-6h-naphthalen-2-yl)ethanone Chemical compound CC(=O)C1=C(C)C=C2C(CC)(C)CCC(C)C2=C1 SSTYKTNTECTUHB-UHFFFAOYSA-N 0.000 description 1
- XRHCAGNSDHCHFJ-UHFFFAOYSA-N Ethylene brassylate Chemical compound O=C1CCCCCCCCCCCC(=O)OCCO1 XRHCAGNSDHCHFJ-UHFFFAOYSA-N 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000006243 chemical reaction Methods 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
- 235000019441 ethanol Nutrition 0.000 description 1
- 239000003205 fragrance Substances 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
- 239000002304 perfume Substances 0.000 description 1
- 239000007858 starting material 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)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
Description
Verfahren zur Herstellung von niedermolekularen 1-Alkyl-6-acetyl-1, 4, 7-trimethyl-1, 2, 3, 4-tetrahydronaphthalinen mit moschusähnlichem Geruch Die Erfindung betrifft die Herstellung neuer Acetylalkyltetrahydronaphthaline mit moschusähnlichem Geruch.Process for the production of low molecular weight 1-alkyl-6-acetyl-1, 4, 7-trimethyl-1, 2, 3, 4-tetrahydronaphthalenes with a musky odor Invention relates to the production of new acetylalkyltetrahydronaphthalenes with a musk-like substance Odor.
Die meisten bekannten moschusartigen Verbindungen fallen unter zwei Gruppen von Stoffen: 1. nitrierte aromatische Verbindungen, wie Xylolmoschus, das ist 2, 4, 6-Trinitro-1, 3-dimethyl-5-tertiäresbutylbenzol, und 2. makrocyclische Ketone, Laktone oder Ester, wie Cyclopentadecanon, Cyclopentadecanolid und Äthylbrassylat.Most known musky compounds fall under two Groups of substances: 1. Nitrated aromatic compounds, such as xylene musk, that is 2, 4, 6-trinitro-1, 3-dimethyl-5-tertiary-butylbenzene, and 2. macrocyclic Ketones, lactones or esters such as cyclopentadecanone, cyclopentadecanolide and ethyl brassylate.
Wenngleich die Glieder in der ersten Gruppe billig herzustellen sind, leiden sie an dem Nachteil, daß sie nicht licht- und alkalibeständig sind, wodurch sie in den Produkten, z. B. 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 them in the products, e.g. B. soap, often cause discoloration. Limbs of second group, although they are sufficiently resistant to light and alkali are difficult 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 aufweisen, während nach dem vorliegenden Verfahren reine Produkte ohne unerwünschte Nebenprodukte erhalten werden.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 undesirable odor, while pure products according to the present process can be obtained without undesirable by-products.
Es wurde nun gefunden, daß man bestimmte neue chemische Verbindungen herstellen kann, welche in ihrem Geruchscharakter moschusähnlich, gegen Licht und Alkalien äußerst beständig und gleichzeitig billig herzustellen und daher nicht übermäßig teuer sind.It has now been found that certain new chemical compounds can be obtained can produce, which in their odor character like musk, against light and Alkalis extremely stable and at the same time cheap to produce and therefore not are excessively expensive.
Die neuen chemischen Verbindungen sind niedermolekulare 1-Allyl-6-acetyl-1, 4, 7-trimethyl-1, 2, 3, 4-tetrahydronaphthaline, in denen der Alkylrest C H3 oder C2 H5 bedeutet. Diese Stoffe sind viskose farblose Öle, löslich in Benzol, Äthylalkohol, Äthylendichlorid und ähnlichen Lösungsmitteln. Sie besitzen als solche einen moschusähnlichen Geruch oder in Lösung und sind gegen Licht und Alkali beständig.The new chemical compounds are low molecular weight 1-allyl-6-acetyl-1, 4, 7-trimethyl-1, 2, 3, 4-tetrahydronaphthalenes, in which the alkyl radical is C H3 or C2 means H5. These substances are viscous, colorless oils, soluble in benzene, ethyl alcohol, Ethylene dichloride and similar solvents. As such, they have a musk-like appearance Odor or in solution and are resistant to light and alkali.
Die neuen Verbindungen werden durch Acetylierung von niedermolekularen 1-Allzyl-1, 4, 7-trimethyl-1, 2, 3, 4-tetrahydronaphthalinen hergestellt, welche nach den in Bull. Soc. Chim. France, 1949, S. 855 bis 857, Compt. rend. hebd., Bd. 226, 1948, S.673 bis 675 und J. Am. Chem. Soc., Bd. 62, 1940, S. 3405 bis 3410, beschriebenen Verfahren nach folgendem Reaktionsschema hergestellt wurden Für die Herstellung der Ausgangsverbindungen wird Schutz im Rahmen der vorliegenden Erfindung nicht beansprucht. Die neuen moschusähnlichen Verbindungen können z. B. in Parfüms, Kosmetika und Seifen verwendet werden.The new compounds are prepared by acetylation of low molecular weight 1-allzyl-1, 4, 7-trimethyl-1, 2, 3, 4-tetrahydronaphthalenes, which are prepared according to the in Bull. Soc. Chim. France, 1949, pp. 855 to 857, Compt. rend. hebd., Vol. 226, 1948, pp. 673 to 675 and J. Am. Chem. Soc., Vol. 62, 1940, pp. 3405 to 3410, were prepared according to the following reaction scheme Protection is not claimed in the context of the present invention for the preparation of the starting compounds. The new musk-like compounds can e.g. B. be used in perfumes, cosmetics and soaps.
Die folgenden Beispiele dienen der Erläuterung der Erfindung.The following examples serve to illustrate the invention.
Beispiel 1 6-Acetyl-1, 1, 4, 7-tetramethyl-1, 2, 3, 4-tetrahydronaphthalin Ein Gemisch aus 22 g Acetylchlorid und 47 g 1, 1, 4, 7-Tetramethyl-1, 2, 3, 4-tetrahydronaphthalin wurde im Verlaufe von einer Stunde unter Rühren und Kühlen zu einer Suspension von 38 g Aluminiumchlorid in 0,4 g Äthylendichlorid gegeben. Die Temperatur wurde auf 20 bis 25° gehalten. Nach der Zugabe wurde das Gemisch noch eine Stunde weiter gerührt, die Lösung auf Eis abgeschreckt, die Äthylendichloridschicht abgetrennt und neutral gewaschen, das Lösungsmittel abdestilliert und das zurückbleibende Öl über 2 g Natriumcarbonat destilliert. Es wurden 47 g farbloses Öl mit starkem Moschusgeruch erhalten, Kp.l = 122°, D25 = 1,5452. Das Produkt war 6-Acetyl-1, 1, 4, 7-tetramethyl-1, 2, 3, 4-tetrahydronaphthalin.Example 1 6-Acetyl-1, 1, 4, 7-tetramethyl-1, 2, 3, 4-tetrahydronaphthalene A mixture of 22 g of acetyl chloride and 47 g of 1, 1, 4, 7-tetramethyl-1, 2, 3, 4-tetrahydronaphthalene was added over the course of one hour with stirring and cooling to a suspension of 38 g of aluminum chloride in 0.4 g of ethylene dichloride. The temperature was kept at 20-25 °. After the addition, the mixture was stirred for a further hour, the solution was quenched on ice, the ethylene dichloride layer was separated off and washed neutral, the solvent was distilled off and the remaining oil was distilled over 2 g of sodium carbonate. 47 g of colorless oil with a strong musk odor were obtained, bp 1 = 122 °, D25 = 1.5452. The product was 6-acetyl-1, 1, 4, 7-tetramethyl-1, 2, 3, 4-tetrahydronaphthalene.
Beispiel 2 6-Acetyl-1, 4, 7-trimethyl-l-ätliyl-1, 2, 3, 4-tetrahydronaphthalin In ähnlicher Weise wie im Beispiel 1 beschrieben, wurde ein Gemisch aus 22 g Acetylchlorid und 50 g 1, 4, 7-Trimethyl-l-äthyl-1, 2, 3, 4-tetrahydronaphthalin im Verlaufe einer Stunde unter Rühren und Kühlen zu einer Suspension von 38 g Aluminiumchlorid in 100 g Äthylendichlorid gegeben, wobei eine Temperatur von 20 bis 25° aufrechterhalten wurde. Nach der Zugabe wurde das Gemisch noch eine Stunde weiter gerührt. Die Lösung wurde auf Eis abgeschreckt, die Ölschicht neutral gewaschen, das Lösungsmittel abdestilliert und das zurückbleibende Öl im Vakuum über 2 g Natriumcarbonat destilliert. Es wurden 47 g 6-Acetyl-1, 4, 7-trimethyl-1-äthyl-1, 2, 3, 4-tetrahydronaphthalin als farbloses Öl mit einem moschusähnlichen Geruch erhalten, Kp.l = 125°, D'5 = 1,0066, 4 = 1,5468.Example 2 6-Acetyl-1, 4, 7-trimethyl-1-ätliyl-1, 2, 3, 4-tetrahydronaphthalene In a manner similar to that described in Example 1, a mixture of 22 g of acetyl chloride and 50 g of 1, 4, 7-Trimethyl-1-ethyl-1, 2, 3, 4-tetrahydronaphthalene was added over the course of one hour with stirring and cooling to a suspension of 38 g of aluminum chloride in 100 g of ethylene dichloride, a temperature of 20 to 25 ° being maintained. After the addition, the mixture was stirred for an additional hour. The solution was quenched on ice, the oil layer was washed neutral, the solvent was distilled off and the remaining oil was distilled in vacuo over 2 g of sodium carbonate. 47 g of 6-acetyl-1, 4, 7-trimethyl-1-ethyl-1, 2, 3, 4-tetrahydronaphthalene were obtained as a colorless oil with a musk-like odor, boiling point 1 = 125 °, D'5 = 1 , 0066, 4 = 1.5468.
Analyse berechnet für Cl, Heg O : C=83,540/, H=9,90"/, gefunden: C=83,53°/10 H=9,540/0Analysis calculated for Cl, Heg O: C = 83.540 /, H = 9.90 "/, found: C = 83.53 ° / 10 H = 9.540 / 0
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US1017162XA | 1955-01-28 | 1955-01-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1017162B true DE1017162B (en) | 1957-10-10 |
Family
ID=22286028
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEG18760A Pending DE1017162B (en) | 1955-01-28 | 1956-01-10 | Process for the preparation of low molecular weight 1-alkyl-6-acetyl-1,4,7-trimethyl-1,2,4-tetrahydronaphthalenes with a musk-like odor |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1017162B (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 DEG18760A patent/DE1017162B/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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