CH102196A - Process for the preparation of phlorisocapronophenone. - Google Patents

Process for the preparation of phlorisocapronophenone.

Info

Publication number
CH102196A
CH102196A CH102196DA CH102196A CH 102196 A CH102196 A CH 102196A CH 102196D A CH102196D A CH 102196DA CH 102196 A CH102196 A CH 102196A
Authority
CH
Switzerland
Prior art keywords
phlorisocapronophenone
preparation
water
ketimide
phloroglucinol
Prior art date
Application number
Other languages
German (de)
Inventor
Paul Prof Dr Karrer
Original Assignee
Paul Prof Dr Karrer
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 Paul Prof Dr Karrer filed Critical Paul Prof Dr Karrer
Publication of CH102196A publication Critical patent/CH102196A/en

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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
    • C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
    • C07C49/825—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups all hydroxy groups bound to the ring
    • 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
    • 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
    • C07C45/42—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by hydrolysis

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Description

  

  Verfahren zur Darstellung von     Phlorisocapronophenono       Nach demselben Verfahren, das im Haupt  patent zur Herstellung von     Resisocaprono-          phenon    beschrieben \worden ist, gelingt es,  aus     Phloroglucin,        Isocapronsäurenitril    und       Halogenwasserstoff    über das entsprechende       Ketimid    das     Phlorisocapronophenon    herzu  stellen. Die Verbindung ist ebenfalls gegen  Würmer wirksam.  



  <I>Beispiel:</I>  Zur Darstellung werden 12,6     gr    trockenes       Phloroglucin,    2     gr    gepulvertes wasserfreies  Zinkchlorid und 10     gr        Isocapronsäurenitril    mit  200 cm' absolutem Äther übergossen und in  die Mischung bis zur Sättigung trockener       Chlorwasserstoff    eingeleitet. Dann lässt man  48 Stunden stehen, wobei das     Ketimidchlor-          hydrat    des     Phlorisocapronophenons    auskristal  lisiert.

   Man giesst die Ätherlösung von den  Kristallen ab, löst letztere in Wasser und  verkocht die wässerige Lösung, wobei teils  in der Hitze, teils beim Erkalten das     Phloriso-          capronophenon    ausfällt.    Es ist in Wasser recht schwer löslich. Die  Lösung färbt sich mit     Ferrichlorid    braunrot.  Das     Keton    kristallisiert mit 1     Mol.        H20,     schmilzt dann bei ca. 104 , in wasserfreiem  Zustand bei 122 .



  Process for the preparation of phlorisocapronophenono Using the same process described in the main patent for the production of resisocapronophenone, it is possible to produce phlorisocapronophenone from phloroglucinol, isocaproic acid nitrile and hydrogen halide via the corresponding ketimide. The compound is also effective against worms.



  <I> Example: </I> To illustrate, 12.6 grams of dry phloroglucinol, 2 grams of powdered anhydrous zinc chloride and 10 grams of isocapronitrile are poured with 200 cm of absolute ether and dry hydrogen chloride is introduced into the mixture until it is saturated. It is then left to stand for 48 hours, during which the ketimide chlorohydrate of phlorisocapronophenone crystallizes out.

   The ether solution is poured off the crystals, the latter is dissolved in water, and the aqueous solution is boiled, the phlorisocapronophenone precipitating partly in the heat and partly on cooling. It is very sparingly soluble in water. The solution turns brownish-red with ferric chloride. The ketone crystallizes with 1 mol. H20, then melts at about 104, in the anhydrous state at 122.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung von Phloriso- capronophenon, darin bestehend, dass man Phloroglucin mit Isocapronsäurenitril und Ha logenwasserstoff zu dem Ketimidchlorhydrat kondensiert und letzteres durch Verkochen mit Wasser zu Phlorisocapronophenon verseift. Das erhaltene Phlorisocapronophenon ist in Wasser schwer löslich, seine Lösung wird auf Zusatz von Ferrichlorid braunrot. Es kristallisiert mit 1 1M1. 1120, schmilzt dann bei ca. 104 , in wasserfreiem Zustand bei 122 . Es soll therapeutische Verwendung finden. PATENT CLAIM: Process for the preparation of phlorisocapronophenone, consisting in that phloroglucinol is condensed with isocaproic acid nitrile and hydrogen halide to give the ketimide chlorohydrate and the latter is saponified to phlorisocapronophenone by boiling with water. The phlorisocapronophenone obtained is sparingly soluble in water; its solution turns brownish-red on addition of ferric chloride. It crystallizes with 1 1M1. 1120, then melts at about 104, in the anhydrous state at 122. It should find therapeutic use.
CH102196D 1921-06-28 1922-11-06 Process for the preparation of phlorisocapronophenone. CH102196A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH97749T 1921-06-28
CH102196T 1922-11-06

Publications (1)

Publication Number Publication Date
CH102196A true CH102196A (en) 1923-12-01

Family

ID=25705309

Family Applications (1)

Application Number Title Priority Date Filing Date
CH102196D CH102196A (en) 1921-06-28 1922-11-06 Process for the preparation of phlorisocapronophenone.

Country Status (1)

Country Link
CH (1) CH102196A (en)

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