CH172358A - Process for the production of a polynuclear, partially hydrogenated ring compound. - Google Patents

Process for the production of a polynuclear, partially hydrogenated ring compound.

Info

Publication number
CH172358A
CH172358A CH172358DA CH172358A CH 172358 A CH172358 A CH 172358A CH 172358D A CH172358D A CH 172358DA CH 172358 A CH172358 A CH 172358A
Authority
CH
Switzerland
Prior art keywords
polynuclear
compound
partially hydrogenated
production
hydrogenated ring
Prior art date
Application number
Other languages
German (de)
Inventor
Gesellschaft Fuer Chemis Basel
Original Assignee
Chem Ind Basel
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 Chem Ind Basel filed Critical Chem Ind Basel
Publication of CH172358A publication Critical patent/CH172358A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J75/00—Processes for the preparation of steroids in general

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

Description

  

  Verfahren zur Herstellung einer mehrkernigen,     teilweise    hydrierten     Ringverbindung.       Es wurde gefunden, dass man zu einer  mehrkernigen, teilweise hydrierten Ringver  bindung der Formel  
EMI0001.0003     
    gelangen kann, wenn man auf die Verbin  dung der Formel  
EMI0001.0004     
    ein sauerwirkendes Kondensationsmittel ein  wirken lässt.  



  Die auf diese Weise erhaltene Verbindung  schmilzt bei     145,5-146,5      und siedet bei  170   unter 0,2 mm Druck. Sie lässt sich  aus wässerigem Alkohol     umkristallisieren;          5-stündiges    Erhitzen mit     Palladiumkohle    bei  320   führt sie in     Chrysen    über.  



  Die neue Verbindung soll als Zwischen  produkt zur Herstellung pharmazeutischer  Stoffe oder von Farbstoffen dienen.    <I>Beispiel:</I>  3     gr    gepulvertes     Nalium    werden mit  75     em3    Benzol und 13     gr        Cyclohexan-l-on-          2-carbonsäureäthylester    versetzt. Nachdem  das Kalium aufgelöst ist, wird mit 19     gr          ss-(Naphthyl-1)-äthylbromid    7 Tage am Rück  fluss gekocht.

   Nach dem Schütteln mit Eis  wasser und Destillation der     ReaktioDspro-          dukte    erhält man das bei<B>208-2120</B> (bei  3 mm) siedende Kondensationsprodukt der  Formel     II.    Der im Vorlauf enthaltene nicht      in Reaktion getretene Anteil des     Bromids     kann regeneriert und für eine neue Konden  sation verwendet werden. Das Kondensations  produkt wird mit der 10 bis 20fachen Menge  Schwefelsäure, hergestellt durch Mischen  gleicher Volumen konzentrierter     SchWefel-          säure    und Wasser, 4 Tage am Rückfuss ge  kocht. Bei der Destillation der mit Äther  ausgezogenen und mit Lauge gewaschenen  Reaktionsprodukte erhält man die oben be  schriebene Verbindung der Formel I.  



  Als saures     .Kondensationsmittel    lassen  sich zum Beispiel auch     Bromwasserstoffsäure,          Phosphorpentogyd,    oder Zinkchlorid verwen  den.



  Process for the production of a polynuclear, partially hydrogenated ring compound. It has been found that a polynuclear, partially hydrogenated Ringver bond of the formula
EMI0001.0003
    can be achieved if you click the compound of the formula
EMI0001.0004
    an acidic condensation agent can act.



  The compound obtained in this way melts at 145.5-146.5 and boils at 170 under 0.2 mm pressure. It can be recrystallized from aqueous alcohol; Heating with palladium-carbon for 5 hours at 320 turns them into chrysene.



  The new compound is intended to serve as an intermediate in the manufacture of pharmaceutical substances or dyes. <I> Example: </I> 3 grams of powdered sodium are mixed with 75 cubic meters of benzene and 13 grams of ethyl cyclohexan-1-one-2-carboxylate. After the potassium has dissolved, 19 gr ss- (naphthyl-1) ethyl bromide is refluxed for 7 days.

   After shaking with ice water and distilling the reaction products, the condensation product of the formula II boiling at 208-2120 (at 3 mm) is obtained. The portion of the bromide that has not reacted in the first run can be regenerated and used for a new condensation. The condensation product is refluxed for 4 days with 10 to 20 times the amount of sulfuric acid, prepared by mixing equal volumes of concentrated sulfuric acid and water. When the reaction products extracted with ether and washed with alkali are distilled, the above-described compound of formula I is obtained.



  Hydrobromic acid, phosphorus pentogide, or zinc chloride, for example, can also be used as acidic condensation agents.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung einer mehr- kernigen,'teilweise hydrierten Ringverbindung der Formel: EMI0002.0009 dadurch gekennzeichnet, dass man auf die Verbindung der Formel: EMI0002.0010 sauerwirkende Kondensationsmittel einwirken lässt. Die auf diese Weise erhaltene Verbindung schmilzt bei 145,h-146,5 und siedet bei 170 unter 2 mm Druck. Sie lässt sich aus wässerigem Alkohol umkristallisieren; 5-stün- diges Erhitzen mit Palladiumkohle bei 320 führt sie in Chrysen über. PATENT CLAIM: Process for the production of a polynuclear, 'partially hydrogenated ring compound of the formula: EMI0002.0009 characterized in that one refers to the compound of the formula: EMI0002.0010 allows acidic condensation agents to act. The compound obtained in this way melts at 145, h-146.5 and boils at 170 under 2 mm pressure. It can be recrystallized from aqueous alcohol; Heating with palladium carbon at 320 for 5 hours converts them into chrysene. Die neue Verbindung soll als Zwischen produkt zur Herstellung pharmazeutischer Stoffe oder von Farbstoffen dienen. UNTERANSPRUCH: Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man als saures Konden sationsmittel Schwefelsäure verwendet. The new compound is intended to serve as an intermediate in the manufacture of pharmaceutical substances or dyes. SUBClaim: Process according to claim, characterized in that sulfuric acid is used as the acidic condensation agent.
CH172358D 1933-06-26 1933-06-26 Process for the production of a polynuclear, partially hydrogenated ring compound. CH172358A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH172358T 1933-06-26

Publications (1)

Publication Number Publication Date
CH172358A true CH172358A (en) 1934-10-15

Family

ID=4423824

Family Applications (1)

Application Number Title Priority Date Filing Date
CH172358D CH172358A (en) 1933-06-26 1933-06-26 Process for the production of a polynuclear, partially hydrogenated ring compound.

Country Status (1)

Country Link
CH (1) CH172358A (en)

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