CH261123A - Process for the preparation of a naphthylpropionic acid. - Google Patents

Process for the preparation of a naphthylpropionic acid.

Info

Publication number
CH261123A
CH261123A CH261123DA CH261123A CH 261123 A CH261123 A CH 261123A CH 261123D A CH261123D A CH 261123DA CH 261123 A CH261123 A CH 261123A
Authority
CH
Switzerland
Prior art keywords
preparation
acid
parts
naphthyl
ether
Prior art date
Application number
Other languages
German (de)
Inventor
Aktiengesellschaft Ciba
Original Assignee
Ciba Geigy
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 Ciba Geigy filed Critical Ciba Geigy
Publication of CH261123A publication Critical patent/CH261123A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
    • C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Description

  

  Verfahren zur Herstellung einer     Naphthylpropionsäure.       Es wurde gefunden, dass man zu einer       Naphthylpropionsäure    gelangen kann, wenn  man ein     a-(6-Methoxy-naphthyl-2)-propyl-          halogenid    mit einem     a-Halogen-isobuttersäure-          ester    in Gegenwart eines halogenabspaltenden  Mittels umsetzt und im erhaltenen Produkt  die veresterte     Carboxylgruppe    verseift.  



  Das bekannte Endprodukt des Verfahrens,  die     ss-(6-Methoxy-naphthyl-2)-,l-äthyl-a,a-di-          methyl-propionsäure    vom Schmelzpunkt 131  bis 133 , ist     oestrogen    wirksam. Es soll thera  peutische Verwendung finden oder als Zwi  schenprodukt zur Herstellung therapeutisch  verwendbarer Verbindungen dienen.  



       Als    halogenabspaltende Mittel verwendet  man z. B. Metalle oder Metallegierungen, z. B.  Zink, Magnesium, Natrium und dergleichen in  Gegenwart von Verdünnungsmitteln, wie  Äther, Benzol,     Toluol    und dergleichen. Die       Verseifung    der veresterten     Carboxylgruppe     kann in an sieh bekannter Weise durchgeführt  werden.  



  <I>Beispiel:</I>  11 Gewichtsteile     a-(6-Methoxy-naphthyl-          2)-propylehlorid    der Formel  
EMI0001.0017     
    werden in 200     Volumteilen    Äther gelöst, mit  9     Volumteilen    a-Brom-isobuttersäuremethyl-         ester    vermischt und in .eine Suspension von  10 Gewichtsteilen Zinkflitter in 100     Volum-          teilen    Äther getropft, wobei bald Reaktion  eintritt. Zur Beendigung derselben kocht man  noch 1/2 Stunde, kühlt ab, giesst auf Eis und  extrahiert das Reaktionsprodukt mit Äther.

    Der Ätherrückstand wird ohne weitere Reini  gung zwecks Hydrolyse der     Carbomethoxy-          gruppe    in einer Mischung von 10 Gewichts  teilen     Kaliumhydroxyd    und 50     Volumteilen     Äthylalkohol im offenen Gefäss auf etwa 160   erhitzt und die gebildete Säure in üblicher  Weise isoliert. Die so erhaltene     ,B-(6-Methoxy-          naphthyl-2)        -ss-äthyl-a,a-dimethyl-propionsäure     der Formel  
EMI0001.0030     
    schmilzt nach     Umlösen    aus verdünntem Me  thanol bei 131 bis 133 .



  Process for the preparation of a naphthylpropionic acid. It has been found that a naphthylpropionic acid can be obtained if an α- (6-methoxy-naphthyl-2) -propyl halide is reacted with an α-halo-isobutyric acid ester in the presence of a halogen-releasing agent and in the product obtained esterified carboxyl group saponified.



  The known end product of the process, ss- (6-methoxy-naphthyl-2) -, l-ethyl-a, a-dimethylpropionic acid with a melting point of 131 to 133, is estrogenically active. It should find therapeutic use or serve as an inter mediate product for the preparation of therapeutically useful compounds.



       As halogen-releasing agents are used, for. B. metals or metal alloys, e.g. B. zinc, magnesium, sodium and the like in the presence of diluents such as ether, benzene, toluene and the like. The saponification of the esterified carboxyl group can be carried out in a manner known per se.



  <I> Example: </I> 11 parts by weight of a- (6-methoxy-naphthyl-2) -propyl chloride of the formula
EMI0001.0017
    are dissolved in 200 parts by volume of ether, mixed with 9 parts by volume of methyl α-bromo-isobutyrate and added dropwise to a suspension of 10 parts by weight of zinc flakes in 100 parts by volume of ether, with reaction soon occurring. To end the same, boil for another 1/2 hour, cool, pour onto ice and extract the reaction product with ether.

    The ether residue is heated to about 160 in an open vessel for hydrolysis of the carbomethoxy group in a mixture of 10 parts by weight of potassium hydroxide and 50 parts by volume of ethyl alcohol and the acid formed is isolated in the usual way. The B- (6-methoxynaphthyl-2) -ss-ethyl-a, a-dimethyl-propionic acid of the formula obtained in this way
EMI0001.0030
    Melts at 131 to 133 after dissolving from dilute methanol.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung einer Naphthyl- propionsäure, dadurch gekennzeichnet, dass man ein a-(6-Methoxy-naphthyl-2)-propyl- halogenid mit einem a-Halogen-isobuttersäure- ester in Gegenwart eines halogenabspaltenden Mittels umsetzt und in dem erhaltenen Pro dukt die veresterte Carboxylgruppe verseift. Claim: A process for the production of a naphthyl propionic acid, characterized in that an α- (6-methoxy-naphthyl-2) propyl halide is reacted with an α-halo-isobutyric acid ester in the presence of a halogen-releasing agent and in the resulting The esterified carboxyl group is saponified.
CH261123D 1947-07-11 1947-07-11 Process for the preparation of a naphthylpropionic acid. CH261123A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH261123T 1947-07-11

Publications (1)

Publication Number Publication Date
CH261123A true CH261123A (en) 1949-04-30

Family

ID=4473810

Family Applications (1)

Application Number Title Priority Date Filing Date
CH261123D CH261123A (en) 1947-07-11 1947-07-11 Process for the preparation of a naphthylpropionic acid.

Country Status (1)

Country Link
CH (1) CH261123A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6608111B1 (en) 1998-06-23 2003-08-19 Southern Illinois University Office Of Research, Development And Administration Method for treating or preventing prostatic conditions

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6608111B1 (en) 1998-06-23 2003-08-19 Southern Illinois University Office Of Research, Development And Administration Method for treating or preventing prostatic conditions

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