CH217938A - Process for the preparation of 2-methyl-3-octadecyl-naphthalene. - Google Patents
Process for the preparation of 2-methyl-3-octadecyl-naphthalene.Info
- Publication number
- CH217938A CH217938A CH217938DA CH217938A CH 217938 A CH217938 A CH 217938A CH 217938D A CH217938D A CH 217938DA CH 217938 A CH217938 A CH 217938A
- Authority
- CH
- Switzerland
- Prior art keywords
- methyl
- octadecyl
- naphthalene
- parts
- preparation
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/782—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic
- C07C49/792—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic containing rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/20—Polycyclic condensed hydrocarbons
- C07C15/24—Polycyclic condensed hydrocarbons containing two 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
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung von 2-biethyl-3-oetadeeyl-naphtalin. Es wurde gefunden, dass 2-Methyl-8-o-cta- decyl-naphtalin dadurch gewonnen werden kann, dass auf ar.-ss-Methyltetralin Stearin säurehalogenid bei Gegenwart von Konden- sationsmittel,n einwirken gelassen., das erhal tene a,r.-2,-Methyl-3-stearyltetralin reduziert und das entstandene ar.-2-Methyl-3-octa- decyl-tetralin dehydriert wird.
Das; neue 2-Methyl-3-octadecyl-naphtalin bildet Kristalle. Es stellt ein Zwischen produkt für die Gewinnung von Arznei mitteln dar. Durch Oxydation erhält man ein Chinon, das eine ausgezeichnete Vitamin K-Wirkung besitzt.
<I>Beispiel:</I> 8 Teile Aluminiumchlorid (pulv.) werden mit 100 Teilen Schwefelkohlenstoff über schichtet, die Mischung in Eiswasser gekühlt und dazu langsam eine Lösung von 8 Teilen Methyltetralin und 18 Teilen Stearinsäure- chlorid in 40 Teilen Schwefelkohlenstoff un ter ständigem Rühren zugetropft. Nach vollendeter Zugabe wird eine Stunde im Eis weiter gerührt und dann zwei Stunden bei Raumtemperatur stehen gelassen.
Nach dem Zersetzen .der Reaktionsmasse durch Ein giessen in. Eiswasser wird der Schwefelkohlen- stoff durchasserdampfd@estillation ent fernt. Beim Erkalten des Destillationsrück- standes erstarrt das- auf dem Wasser sehwim- mende 01 zu einer festen. weissen Decke. Es wird mit Äther ausgezogen und der Rück stand des Ätherextraktes aus Äthanol um kristallisiert.
Die erhaltenen Kristalle wer den nochmals in Äther gelöst und mit stark verdünnter Lauge ausgeschüttelt. Auf diese Weise können geringe Mengen vorhandener Stearinsäure entfernt werden. Nach mehr maligem LTmkristallisieren aus Äthanol blieb der Schmelzpunkt .des ar.-2-Methyl-3-stearyl- tetTalins- konstant bei 64' C.
12 Teile ar.-2f-Methyl-3-stearyltetralin werden mit<B>100</B> Teilen frischamalgamiertem, gekörntem Zink in einer Mischung von 170 Teilen Äthanol und 330 Teilen konzen- trierter Salzsäure am R.iiekflusskiih.ler wäh rend 24 Stunden kräftig im Sieden gehalten; hierauf wird das Reaktionsgemisch in Wasser gegossen, ausgeäthert, isoliert und erneut der Reduktion mit. amalgamiertem Zink unter warfen.
Das erhaltene ar.-2-llethvl; 3-octa- decyl-tetralin ist eine feste weisse Masse, die aus Äthanol umkristallisiert wird. Sie achmilzt bei 51-54' C.
5 Teile des ar.-2-Methyl-3-octadecyl-t.etra- l,ins werden mit 0,85 Teilen Schwefel wäh rend 3 Stunden auf 205-220" C (Badtempe- ratur) erhitzt. Nach dem Erkalten wird die Reaktionsmasse mit 100 Teilen 1 (l 7o iger Soda.lösung aufgekocht und mit Äther ausge zogen. Aus der Ätherlösung erhält man ein braunrotes Öl, das sofort erstarrt.
Die Rei nigung des entstandenen 2-llethyl-3-octa- (lecyl-naphtalins geschieht durch Destillation über Natrium und nachfolgender Kristalli- sation aus Athanol.
Process for the preparation of 2-bidhyl-3-oetadeeyl-naphthalene. It has been found that 2-methyl-8-o-ctadecyl-naphthalene can be obtained by allowing stearic acid halide to act on ar.-ss-methyltetraline in the presence of a condensing agent, n., The obtained a, r-2-methyl-3-stearyltetralin is reduced and the ar-2-methyl-3-octadecyl-tetralin formed is dehydrated.
The; new 2-methyl-3-octadecyl-naphthalene forms crystals. It is an intermediate product for the production of medicines. Oxidation produces a quinone that has an excellent vitamin K effect.
<I> Example: </I> 8 parts of aluminum chloride (powder) are coated with 100 parts of carbon disulfide, the mixture is cooled in ice water and a solution of 8 parts of methyltetralin and 18 parts of stearic acid chloride in 40 parts of carbon disulfide is slowly added added dropwise with constant stirring. After the addition is complete, stirring is continued for one hour in ice and then left to stand for two hours at room temperature.
After the reaction mass has decomposed by pouring it into ice water, the carbon disulfide is removed by steam distillation. When the distillation residue cools down, the oil floating on the water solidifies into a solid one. white ceiling. It is extracted with ether and the residue of the ether extract crystallized from ethanol.
The crystals obtained are dissolved again in ether and extracted with very dilute lye. In this way, small amounts of any stearic acid present can be removed. After recrystallizing several times from ethanol, the melting point of the ar-2-methyl-3-stearyl-tet taline remained constant at 64 ° C.
12 parts of ar.-2f-methyl-3-stearyltetralin are mixed with 100 parts of freshly amalgamated, granular zinc in a mixture of 170 parts of ethanol and 330 parts of concentrated hydrochloric acid on the river during 24 Kept vigorously boiling for hours; the reaction mixture is then poured into water, extracted with ether, isolated and again with the reduction. amalgamated zinc.
The obtained ar.-2-llethvl; 3-octadecyl-tetralin is a solid white mass that is recrystallized from ethanol. It melts at 51-54 'C.
5 parts of ar.-2-methyl-3-octadecyl-t.etra- l, ins are heated with 0.85 parts of sulfur for 3 hours to 205-220 "C (bath temperature). After cooling, the Reaction mass with 100 parts 1 (7o strength soda solution boiled and extracted with ether. A brown-red oil is obtained from the ethereal solution, which solidifies immediately.
The 2-llethyl-3-octa- (lecyl-naphthalene) formed is purified by distillation over sodium and subsequent crystallization from ethanol.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH215656T | 1940-02-09 | ||
| CH217938T | 1940-02-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH217938A true CH217938A (en) | 1941-11-15 |
Family
ID=25725727
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH217938D CH217938A (en) | 1940-02-09 | 1940-02-09 | Process for the preparation of 2-methyl-3-octadecyl-naphthalene. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH217938A (en) |
-
1940
- 1940-02-09 CH CH217938D patent/CH217938A/en unknown
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