CH221523A - Process for the preparation of a new ester. - Google Patents

Process for the preparation of a new ester.

Info

Publication number
CH221523A
CH221523A CH221523DA CH221523A CH 221523 A CH221523 A CH 221523A CH 221523D A CH221523D A CH 221523DA CH 221523 A CH221523 A CH 221523A
Authority
CH
Switzerland
Prior art keywords
agent
preparation
oxyphenyl
butyrylating
new ester
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 CH221523A publication Critical patent/CH221523A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
    • C07C69/22—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety
    • C07C69/28—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety esterified with dihydroxylic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/205—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic, containing only six-membered aromatic rings as cyclic parts with unsaturation outside the rings
    • C07C39/21—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic, containing only six-membered aromatic rings as cyclic parts with unsaturation outside the rings with at least one hydroxy group on a non-condensed ring
    • C07C39/215—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic, containing only six-membered aromatic rings as cyclic parts with unsaturation outside the rings with at least one hydroxy group on a non-condensed ring containing, e.g. diethylstilbestrol
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
    • C07C69/12—Acetic acid esters
    • C07C69/16—Acetic acid esters of dihydroxylic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/96—Esters of carbonic or haloformic acids

Landscapes

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

Description

  

  Verfahren zur Darstellung eines neuen Esters.    Es wurde gefunden, dass man zu einem  neuen Ester gelangen kann, wenn man     3,4-          Di-(p-oxyphenyl)-hexadien-(2,4)    der Formel:  
EMI0001.0003     
    mit einem     Butyrylierungsmittel    behandelt.  Geeignete     butyrylierende    Mittel sind z. B.  



  die Buttersäure selbst, ihre     Halogenide    oder  Ester mit niederen Alkoholen     (Umesterung),     ihr     Anhydrid    sowie auch das von ihr abge  leitete Feten. Man kann die Reaktion gege  benenfalls bei Gegenwart eines Verdünnungs  mittels ausführen, z. B. eines indifferenten  Mittels sowie mit oder unter Ausschluss von  katalytisch wirkenden Zusätzen, z. B.

   Säuren,  Salzen anorganischer und organischer Säuren  oder tertiären Basen wie     Pyridin    oder     Chinolin.       Die neue Verbindung, das     3,4-Di-(p-oxy-          phenyl)-hexadien-(2,4)-dibutyrat,    bildet farb  lose     Kristalle.    Es zeigt gegenüber den bekann  ten hormonal wirksamen     Verbindungen    ohne       Steroid-Charakter    eine     protrahiertere    Wirkung       im        Oestrus-    und     LTteruswachstumstest        und    soll  deshalb therapeutische Verwendung     finden.     



       Beispiel:     1 Teil     3,4-Di-(p-oxyphenyl)-hexadien-(2,4)     wird in 15 Teilen     Pyridin        und    5     Teilen    Butter  säureanhydrid einige Zeit auf<B>110'</B> erhitzt.  Hierauf lässt man erkalten und versetzt das  Gemisch mit Wasser, wobei sich ein 01 aus  scheidet. Dieses wird in Äther     aufgenommen     und nacheinander mit     n-Schwefelsäure,    Was  ser und     n,110-Natronlauge    gewaschen. Nach  dem Verdunsten des Äthers erhält man das       Dibutyrat.    Es wird aus wässerigem     Äthanolum     gelöst bis sich farblose Kristalle ergeben.



  Process for the preparation of a new ester. It has been found that a new ester can be obtained if 3,4-di- (p-oxyphenyl) -hexadiene- (2,4) of the formula:
EMI0001.0003
    treated with a butyrylating agent. Suitable butyrylating agents are e.g. B.



  butyric acid itself, its halides or esters with lower alcohols (transesterification), its anhydride and also the fetus derived from it. You can, if necessary, carry out the reaction in the presence of a diluent, e.g. B. an indifferent agent and with or with the exclusion of catalytically active additives such. B.

   Acids, salts of inorganic and organic acids or tertiary bases such as pyridine or quinoline. The new compound, 3,4-di- (p-oxyphenyl) -hexadiene- (2,4) -dibutyrate, forms colorless crystals. Compared to the known hormonally active compounds without steroid character, it shows a more protracted effect in the oestrus and LTterus growth test and should therefore be used therapeutically.



       Example: 1 part of 3,4-di- (p-oxyphenyl) -hexadiene- (2,4) is heated to <B> 110 '</B> for some time in 15 parts of pyridine and 5 parts of butyric anhydride. It is then allowed to cool and water is added to the mixture, an 01 separating out. This is taken up in ether and washed successively with n-sulfuric acid, what water and n.110 sodium hydroxide solution. The dibutyrate is obtained after the ether has evaporated. It is dissolved from aqueous ethanol until colorless crystals result.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines neuen Esters, dadurch gekennzeichnet, dass man 3,4-Di-(p-oxyphenyl)-hexadien-(2,4) derFormel EMI0002.0003 mit einem Butyrylierungsmittel behandelt. Die neue Verbindung, das 3,4-Di-(p-oxy- phenyl)-hexadieii-(2,4)-dibutyrat bildet farb lose Kristalle. Claim: Process for the preparation of a new ester, characterized in that 3,4-di- (p-oxyphenyl) -hexadiene- (2,4) of the formula EMI0002.0003 treated with a butyrylating agent. The new compound, 3,4-di- (p-oxyphenyl) -hexadieii- (2,4) -dibutyrate, forms colorless crystals. Es zeigt gegenüber den bekann ten hormonal wirksamen Verbindungen ohne Steroid-C1iar;ikter eine protrahiertere "Wirkung im Oestrus- und Z teruswaehstumstest und soll deshalb therapeutische Verwendung finden. UNTERANSPRÜCHE: 1. Verfahren nach Patentanspruch, dadurch gekennzeichnet, dah als butyryliereiides Mittel Buttersäureanhydrid verwendet wird. 2. Compared to the known hormonally active compounds without steroid C1iar; icter it shows a more protracted "effect in the oestrus and cereus growth test and is therefore intended to be used therapeutically. SUBClaims: 1. Method according to patent claim, characterized in that butyric anhydride is used as the butyrylic agent 2. Verfahren nach Patentanspruch, dadurch gekennzeichnet, dah als butyry lierendes -Mittel ein Buttersäurehalogenid verwendet wird. A method according to claim, characterized in that a butyric acid halide is used as the butyrylating agent.
CH221523D 1938-07-21 1938-07-21 Process for the preparation of a new ester. CH221523A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH221523T 1938-07-21
CH217885T 1938-12-27

Publications (1)

Publication Number Publication Date
CH221523A true CH221523A (en) 1942-05-31

Family

ID=25726075

Family Applications (1)

Application Number Title Priority Date Filing Date
CH221523D CH221523A (en) 1938-07-21 1938-07-21 Process for the preparation of a new ester.

Country Status (1)

Country Link
CH (1) CH221523A (en)

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