CH213346A - Process for the preparation of 2-phytyl-naphthoquinone-1,4. - Google Patents

Process for the preparation of 2-phytyl-naphthoquinone-1,4.

Info

Publication number
CH213346A
CH213346A CH213346DA CH213346A CH 213346 A CH213346 A CH 213346A CH 213346D A CH213346D A CH 213346DA CH 213346 A CH213346 A CH 213346A
Authority
CH
Switzerland
Prior art keywords
naphthoquinone
phytyl
preparation
derivatives
naphthylethyl
Prior art date
Application number
Other languages
German (de)
Inventor
F Hoffmann- Aktiengesellschaft
Original Assignee
Hoffmann La Roche
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche
Publication of CH213346A publication Critical patent/CH213346A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C50/00—Quinones
    • C07C50/26—Quinones containing groups having oxygen atoms singly bound to carbon atoms
    • C07C50/32—Quinones containing groups having oxygen atoms singly bound to carbon atoms the quinoid structure being part of a condensed ring system having two rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C46/00—Preparation of quinones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C46/00—Preparation of quinones
    • C07C46/02—Preparation of quinones by oxidation giving rise to quinoid structures
    • C07C46/04—Preparation of quinones by oxidation giving rise to quinoid structures of unsubstituted ring carbon atoms in six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C50/00—Quinones
    • C07C50/10—Quinones the quinoid structure being part of a condensed ring system containing two rings
    • C07C50/14—Quinones the quinoid structure being part of a condensed ring system containing two rings with unsaturation outside the ring system, e.g. vitamin K1

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

       

  Verfahren zur Darstellung von     2-Phytyl-naphtochinon-1,4.       Es     wurde        gefunden,    dass durch Behand  lung von     Naphtalinabkömmlingen,    welche     in     der     P-Stellung    eine 15 oder mehr     C-Atome     enthaltende     aliphatische        Terpenkette    tragen  und gegebenenfalls weiter substituiert sind,  mit oxydierenden     Mitteln    neue     Naphtochinon-          abkömmlinge    erhalten werden.  



  Von diesen     Naphtochinonabkömmlingen     sind diejenigen von besonderem Interesse,    welche     in    der     Terpenkette        ungesättigt        sind,     beispielsweise     zwischen    dem     ss-    und dem r  ständigen     gohlenstoffatom    eine Doppelbin  dung besitzen.

   Zu solchen Verbindungen     kamt     man     in    besonderer     Ausgestaltung    des vor  stehend erwähnten     allgemeinen    Verfahrens  dadurch gelangen, dass man     Verbindungen     der allgemeinen Formel  
EMI0001.0026     
    worin R     Wasserstoff    oder     Alkyl,        g    Wasser  stoff oder Halogen     und    Y Halogen oder     Hydr-          oxyl    bedeuten,

   oxydiert und     zwischen    dem F  und dem     7--ständigen        C-Atom    der Seitenkette  durch Wasser-     bezw.    Halogenabspaltung eine  Doppelbindung herstellt. Man kann auch       direkt        P-Phytylnaphtalin    oder dessen     Alkyl-          derivate    durch Behandlung mit     oxydierenden            Mitteln    in die entsprechenden     Naphtochinon-          abkömmlinge    überführen.  



  Gegenstand des     vorliegenden    Patentes ist  ein Verfahren zur Darstellung von     2-Phytyl-          naphtochinon-1,4,    welches     dadurch    gekenn  zeichnet ist, dass man     (2-A-Naphtyläthyl)-          (4,8,12-trimethyltridecyl)-methylcarbinol    zu  nächst mit     oxydierenden        Mitteln    und hier-      auf mit wasserentziehenden     Mitteln    behan  delt.  



  Das bisher unbekannte     2-Pliytyl-naphto-          chinon-1,4    ist ein lichtempfindliches, gelbes  <B>01,</B> das erst bei tiefen Temperaturen fest  wird. Es besitzt ein charakteristisches Ad  sorptionsspektrum und soll pharmazeutische  Verwendung finden.    <I>Beispiel:</I>  14 g     (2-i3-Naphtyläthyl)-(4,8,12-trimethyl-          tridecy        1)-metliylcai-binol    werden in 100     eins     Eisessig gelöst und bei 60   mit einer Lösung  von 20 g Chromsäure in 30 ein' 50      /(,iger     Essigsäure vereinigt.

   Man hält. die Reaktions  mischung     ;'2    bis     1'/     Stunden bei<B>60',</B> ver  dünnt hierauf mit Wasser,     äthert    aus und  reinigt das erhaltene     Kondensationsprodukt     von der Formel  
EMI0002.0013     
    durch     Chromatographieren    an     Zinkoarbonat.     Hierauf entzieht man dem Kondensations  produkt durch Behandlung mit Phenyliso-         cyanat        11 < 7o1        H20    in der Seitenkette.  



  Das 2 -     Phytyl    -     naphtochinon    -1,4 von der  Formel  
EMI0002.0021     
    wird durch     Chromatographie    gereinigt (Ad  sorptionsmittel     Zinkcarbonat).  



  Process for the preparation of 2-phytyl-naphthoquinone-1,4. It has been found that by treating naphthalene derivatives which have an aliphatic terpene chain containing 15 or more carbon atoms in the P position and are optionally further substituted, new naphthoquinone derivatives are obtained with oxidizing agents.



  Of these naphthoquinone derivatives, those which are unsaturated in the terpene chain, for example have a double bond between the s and r carbon atoms, are of particular interest.

   In a particular embodiment of the above-mentioned general process, such compounds are obtained by using compounds of the general formula
EMI0001.0026
    in which R is hydrogen or alkyl, g is hydrogen or halogen and Y is halogen or hydroxyl,

   oxidized and between the F and the 7 - carbon atom of the side chain by water or. Elimination of halogen creates a double bond. P-phytylnaphthalene or its alkyl derivatives can also be converted directly into the corresponding naphthoquinone derivatives by treatment with oxidizing agents.



  The subject of the present patent is a process for the preparation of 2-phytyl-naphthoquinone-1,4, which is characterized in that (2-A-naphthylethyl) - (4,8,12-trimethyltridecyl) -methylcarbinol with the next oxidising agents and then treated with dehydrating agents.



  The previously unknown 2-pliytyl-naphthoquinone-1,4 is a light-sensitive, yellow <B> 01 </B> that only solidifies at low temperatures. It has a characteristic adsorption spectrum and is intended to be used in pharmaceuticals. <I> Example: </I> 14 g (2-i3-naphthylethyl) - (4,8,12-trimethyl-tridecy 1) -metliylcai-binol are dissolved in 100 one glacial acetic acid and at 60 with a solution of 20 g Chromic acid combined in 30% acetic acid.

   One holds. the reaction mixture; '2 to 1' / hours at <B> 60 ', </B> then dilutes with water, ethers out and purifies the resulting condensation product of the formula
EMI0002.0013
    by chromatography on zinc carbonate. The side chain is then removed from the condensation product by treatment with phenyl isocyanate 11 <701 H20.



  The 2-phytyl-naphthoquinone -1.4 of the formula
EMI0002.0021
    is purified by chromatography (adsorbent zinc carbonate).

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung von 2-Pliy ty 1- naphtochinori -1,4, dadurch gekennzeichnet, dass man (2-;3-Naphtyläthyl)-(4,8,12-trimethyl- tridecyl)-methylcarbinol zunächst mit oxydie renden und hierauf mit wasserentziehenden Mitteln behandelt. Das bisher unbekannte 2-Phytyl-naphto- cliinon-1,4 ist ein lichtempfindliches, gelbes <B>01,</B> das erst bei tiefen Temperaturen fest wird. PATENT CLAIM: Process for the preparation of 2-Pliy ty 1- naphtochinori -1,4, characterized in that (2-; 3-naphthylethyl) - (4,8,12-trimethyltridecyl) -methylcarbinol initially with oxidizing and then treated with dehydrating agents. The previously unknown 2-phytyl-naphtho-cliinone-1,4 is a light-sensitive, yellow <B> 01 </B> that only solidifies at low temperatures. Es besitzt ein charakteristisches Adsorptions- spektrum und soll pharmazeutische Y erwen- dung finden. It has a characteristic adsorption spectrum and is intended to be used in pharmaceuticals.
CH213346D 1939-07-26 1939-07-26 Process for the preparation of 2-phytyl-naphthoquinone-1,4. CH213346A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH213346T 1939-07-26

Publications (1)

Publication Number Publication Date
CH213346A true CH213346A (en) 1941-01-31

Family

ID=4448199

Family Applications (1)

Application Number Title Priority Date Filing Date
CH213346D CH213346A (en) 1939-07-26 1939-07-26 Process for the preparation of 2-phytyl-naphthoquinone-1,4.

Country Status (1)

Country Link
CH (1) CH213346A (en)

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