CH222169A - Process for the preparation of a condensation product from 3,5-diethyl-hydroquinone and phytyl halides. - Google Patents

Process for the preparation of a condensation product from 3,5-diethyl-hydroquinone and phytyl halides.

Info

Publication number
CH222169A
CH222169A CH222169DA CH222169A CH 222169 A CH222169 A CH 222169A CH 222169D A CH222169D A CH 222169DA CH 222169 A CH222169 A CH 222169A
Authority
CH
Switzerland
Prior art keywords
sep
diethyl
phytyl
halides
hydroquinone
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 CH222169A publication Critical patent/CH222169A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
    • C07D311/70—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with two hydrocarbon radicals attached in position 2 and elements other than carbon and hydrogen in position 6
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
    • C07D311/70—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with two hydrocarbon radicals attached in position 2 and elements other than carbon and hydrogen in position 6
    • C07D311/72—3,4-Dihydro derivatives having in position 2 at least one methyl radical and in position 6 one oxygen atom, e.g. tocopherols

Landscapes

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

Description

  

      Yerfahren    zur Darstellung eines     liondensationsproduktes    aus     3,ä-Diäthyl-hydrochinon     und     Phytylhalogeniden.       Nach dem Verfahren des Hauptpatentes  wird eine Verbindung mit Vitamin     E-"N,#Tir-          kung    dadurch gewonnen, dass man     Trimethyl-          hydrochinon    in     einem    indifferenten     Lösungs-          mitted    auf     Phytylihal,

  ogenide    bei Gegen  wart     eines        Kondensationsmittels        einwirken     lässt. Es wurde ferner gefunden,     dass    man zu  Homologen der     dl=To:

  copherol@e    gelangen  kann, wenn man auf     a.11ylsubstituiei-te          HydrochinonCerivate,    deren     Alkylgruppen     teils     Methyl-,    teils höhere     Alkylgruppen          odQr    ausschliesslich höhere     Al.kylgruppen          sind,        Phytol    oder     Derivate    desselben in An  wesenheit von sauren Kondensationsmitteln  einwirken lässt.

   Für .die Ausführung des    Verfahrens können sowohl     Phytol    selbst als  auch Derivate desselben, wie beispielsweise       P.hytylmo.no-    oder     -dihalogenid,--    oder auch       Isophytol        verwendet    werden.  



  Gegenstand des vorliegenden     Patentes    ist  ein Verfahren zur Darstellung eines Konden  sationsproduktes aus     3,5-Diäthyl-hydrochi-          non    und     Phytylhalogeniden,    welches dadurch  gekennzeichnet ist, dass     3,5-Diäthyl-hydro-          chinon    und     Phytylhalogenide    bei Gegen  wart eines sauren     Kondensationsmittels    auf  einandereinwirken gelassen werden.  



  Das bisher     unbekannte        2-Methyl-5,7-@di-          äthyl    - 2 -     (4',8',12'-trimethyl-trideeyl)    - 6 -     oxy-          chroman    von der Formel  
EMI0001.0047     
    
EMI0002.0001     
  
    stellt <SEP> ein <SEP> wenig <SEP> gefärbtes, <SEP> viskoses <SEP> ö1 <SEP> von
<tb>  starkem <SEP> Reduktionsvermögen <SEP> dar. <SEP> Die <SEP> Ver  bindung <SEP> besitzt <SEP> ein <SEP> Absoi@ptionsma.xinitim <SEP> bei
<tb>  zirka. <SEP> 290 <SEP> m,cr <SEP> und <SEP> ein <SEP> Alisoi@ptionsmiiiimiiin
<tb>  bei <SEP> <I>255 <SEP> my.</I>
<tb>  



  Die <SEP> neue <SEP> Verbindung <SEP> vermag <SEP> im <SEP> biolo  gischen <SEP> Versuch <SEP> die <SEP> Wirkumr <SEP> des <SEP> Vitamin <SEP> E
<tb>  auszuüben; <SEP> sie <SEP> soll <SEP> als <SEP> Arzneimittel <SEP> vei- -en  det <SEP> werden.
<tb>  



  <I>Beispiel:</I>
<tb>  1,7 <SEP> Teile <SEP> 3,5-Diätliyl-liydrochinon, <SEP> 4,8
<tb>  Teile <SEP> Phytylbromid, <SEP> 1 <SEP> Teil <SEP> wasserfreies
<tb>  Zinkchlorid <SEP> und <SEP> 30 <SEP> Teile <SEP> trockenes <SEP> Benzin
<tb>  werden <SEP> 1 <SEP> ? <SEP> Stunden <SEP> auf <SEP> dem <SEP> Wasserbad <SEP> er  wärmt.

   <SEP> iKach <SEP> aufeinanderfolgendem <SEP> Aus  schütteln <SEP> der <SEP> Reaktionsinacse <SEP> finit <SEP> Wasser,
<tb>  Lauge <SEP> und <SEP> Wasser <SEP> wird <SEP> die <SEP> Benzinschicht            betrockiiet.    Das in letzterer enthaltene Kon  densationsprodukt wird durch     Adsorption     an Aluminiumoxyd     gereinigt.    Durch     Elution     mit einem     Metliatiol-Äthergeniisch    wird ein       wenig        gefärbtes,        viskoses   <B>01</B> erhalten.



      Yerfahren for the preparation of a liondensationsproduktes from 3, a-diethyl-hydroquinone and phytyl halides. According to the process of the main patent, a compound with vitamin E- "N, # tinting is obtained by adding trimethyl-hydroquinone in an inert solvent to Phytylihal,

  ogenide can act in the presence of a condensation agent. It was also found that homologues of the dl = To:

  Copherols can be achieved if a.11ylsubstituiei-te hydroquinone derivatives, the alkyl groups of which are partly methyl, partly higher alkyl groups or exclusively higher alkyl groups, phytol or derivatives thereof are allowed to act in the presence of acidic condensing agents.

   Both phytol itself and derivatives thereof, such as, for example, P.hytylmo.no- or dihalide, or isophytol, can be used for carrying out the method.



  The subject of the present patent is a process for the preparation of a condensation product from 3,5-diethyl-hydroquinone and phytyl halides, which is characterized in that 3,5-diethyl-hydroquinone and phytyl halides act on one another in the presence of an acidic condensation agent be left.



  The previously unknown 2-methyl-5,7- @ diethyl - 2 - (4 ', 8', 12'-trimethyl-trideeyl) - 6 - oxychroman of the formula
EMI0001.0047
    
EMI0002.0001
  
    sets <SEP> a <SEP> little <SEP> colored, <SEP> viscous <SEP> ö1 <SEP> of
<tb> strong <SEP> reducing power <SEP>. <SEP> The <SEP> connection <SEP> has <SEP> an <SEP> Absoi@ptionsma.xinitim <SEP> at
<tb> approx. <SEP> 290 <SEP> m, cr <SEP> and <SEP> a <SEP> Alisoi @ ptionsmiiiimiiin
<tb> at <SEP> <I> 255 <SEP> my. </I>
<tb>



  The <SEP> new <SEP> compound <SEP> is capable of <SEP> in the <SEP> biological <SEP> trial <SEP> the <SEP> effect <SEP> of the <SEP> vitamin <SEP> E
exercise <tb>; <SEP> it <SEP> should <SEP> be avoided as <SEP> drug <SEP> <SEP>.
<tb>



  <I> Example: </I>
<tb> 1.7 <SEP> parts <SEP> 3,5-dietliyl-liydroquinone, <SEP> 4.8
<tb> parts <SEP> phytyl bromide, <SEP> 1 <SEP> part <SEP> anhydrous
<tb> zinc chloride <SEP> and <SEP> 30 <SEP> parts <SEP> dry <SEP> gasoline
<tb> will <SEP> 1 <SEP>? <SEP> hours <SEP> on <SEP> the <SEP> water bath <SEP> is heated.

   <SEP> iKach <SEP> successive <SEP> shaking <SEP> the <SEP> reaction axis <SEP> finite <SEP> water,
<tb> Lye <SEP> and <SEP> water <SEP> will <SEP> affect the <SEP> gasoline layer. The condensation product contained in the latter is purified by adsorption on aluminum oxide. A slightly colored, viscous <B> 01 </B> is obtained by elution with a Metliatiol-Äthergeniisch.

Claims (1)

EMI0002.0010 PATEN <SEP> TANSPRUCII <tb> Verfahren <SEP> zur <SEP> Darstellung <SEP> eines <SEP> Konden sationsproduktes <SEP> aus <SEP> 3,5-Diäthyl-hydi-oehi non <SEP> und <SEP> Phytylhalogeniden, <SEP> dadurch <SEP> ge kennzeichnet, <SEP> dass <SEP> 3,5-Diäthyl-hydroehinon <tb> und <SEP> Pbyt.ylbalogenid'@e <SEP> frei <SEP> Gegenwart <SEP> eines <tb> sauren <SEP> Kondensationsmittels <SEP> aufeinander <SEP> ein wirken <SEP> gelassen <SEP> wenden. <tb> Das <SEP> bisher <SEP> unbekannte <SEP> 2-Methyl-5,7-di ii <SEP> thyl <SEP> - <SEP> 2 <SEP> -(4'.8'.12'-t <SEP> ri <SEP> methy <SEP> l-tridecyl) <SEP> -fi <tb> cbronian <SEP> von <SEP> der <SEP> Formel EMI0002.0011 EMI0002.0012 stellt <SEP> ein <SEP> wenig <SEP> gefärbte: EMI0002.0010 PATEN <SEP> TANSPRUCII <tb> Method <SEP> for the <SEP> representation <SEP> of a <SEP> condensation product <SEP> made of <SEP> 3,5-diethyl-hydi-oehi non <SEP> and <SEP> phytyl halides, <SEP> characterized by <SEP>, <SEP> that <SEP> 3,5-diethyl-hydroehinone <tb> and <SEP> Pbyt.ylbalogenid'@e <SEP> free <SEP> present <SEP> one <tb> acidic <SEP> condensation agent <SEP> act on each other <SEP> <SEP> let <SEP> turn. <tb> The <SEP> previously <SEP> unknown <SEP> 2-methyl-5,7-di ii <SEP> thyl <SEP> - <SEP> 2 <SEP> - (4'.8'.12 ' -t <SEP> ri <SEP> methy <SEP> l-tridecyl) <SEP> -fi <tb> cbronian <SEP> from <SEP> of the <SEP> formula EMI0002.0011 EMI0002.0012 sets <SEP> a <SEP> little <SEP> colored: , <SEP> viskoses <SEP> (11 <SEP> von <tb> starkem <SEP> Reduktionsvermögen <SEP> dar. <SEP> Die <SEP> V#@r bindung <SEP> besitzt <SEP> ein <SEP> Al@sorptionsmaxiinuni EMI0002.0013 bei <SEP> zirka. <SEP> 290 <SEP> inp <SEP> mid <SEP> ein <SEP> Absorptionsmini inuni <SEP> bei <SEP> <I>255 <SEP> mli.</I> , <SEP> viscous <SEP> (11 <SEP> from <tb> strong <SEP> reducing power <SEP>. <SEP> The <SEP> V # @ r bond <SEP> has <SEP> a <SEP> Al @ sorption maxiinuni EMI0002.0013 at <SEP> approx. <SEP> 290 <SEP> inp <SEP> mid <SEP> a <SEP> absorption mini inuni <SEP> at <SEP> <I> 255 <SEP> mli. </I>
CH222169D 1939-03-08 1939-03-08 Process for the preparation of a condensation product from 3,5-diethyl-hydroquinone and phytyl halides. CH222169A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH222169T 1939-03-08
CH205896T 1939-03-08

Publications (1)

Publication Number Publication Date
CH222169A true CH222169A (en) 1942-06-30

Family

ID=25724237

Family Applications (1)

Application Number Title Priority Date Filing Date
CH222169D CH222169A (en) 1939-03-08 1939-03-08 Process for the preparation of a condensation product from 3,5-diethyl-hydroquinone and phytyl halides.

Country Status (1)

Country Link
CH (1) CH222169A (en)

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