CH137144A - Process for the preparation of a basic phenol alkyl ether. - Google Patents

Process for the preparation of a basic phenol alkyl ether.

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Publication number
CH137144A
CH137144A CH137144DA CH137144A CH 137144 A CH137144 A CH 137144A CH 137144D A CH137144D A CH 137144DA CH 137144 A CH137144 A CH 137144A
Authority
CH
Switzerland
Prior art keywords
preparation
alkyl ether
methyl ester
basic phenol
phenol alkyl
Prior art date
Application number
Other languages
German (de)
Inventor
Aktiengesellsc Farbenindustrie
Original Assignee
Ig Farbenindustrie Ag
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 Ig Farbenindustrie Ag filed Critical Ig Farbenindustrie Ag
Publication of CH137144A publication Critical patent/CH137144A/en

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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Description

  

      Verfahren    zur Darstellung eines     basischen        Plienoialkyläthers.       Im     Hauptpatent    ist ein Verfahren zur       Darstellung    eines neuen basischen     Phenol-          allzyläthers        (2-.        6-Dim:ethoxy-4,-,allyl-phenyl          diäthyla-minoäthyläther)    beschrieben.  



  Es zeigt sieh nun, dass man einen neuen       Phenolalkyläther    erhält, wenn man     5-Allyl..          o-kresotinsäuremethylester    (OH,     CH,    =<B>2.3)</B>  entsprechend dem     Verfahren    des Haupt  patentes mit     Diäthylaminoäthylchlorid    zum  2-     (c)-Diäithyl,aminoärtho@xy)"-8-merthyl-5-.aJ,lyl-          benzoesäuremethylester    umsetzt.  



  Das Produkt soll als     Lolca.lanä"thetikum          Verwendung    finden.  



  <I>Beispiel:</I>  75     Gewichtsteile        5-Allyl-o-kresotinsäure-          methvjester    (OH,     CH,    = 2.     ä)    werden zu  sammen mit     einer    Auflösung von 8 Gewichts  teilen Natrium     in.    200     Gewichtsteilen    Alkohol  und 75     Gewichtsteilen        Diäthylaminoäthyl-          eh1oiid    einige Zeit gekocht.

   Nach dem     Ab,de.-          still.ieren    des Alkohols nimmt man den Rück-    stand     in    verdünnter     :Salzsäure    .auf,     schüttelt    mit  Äther     aus    und versetzt ,die     ausgeätherte    wäs  serige     Lösung        bis    zur     alkalischen    Reaktion  mit     Natronlauge.    Das dadurch abgeschiedene       0l        wird    abgetrennt, getrocknet     und        destil-          liert.     



  Unter 1 mm Druck siedet der so erhal  tene     2-(co-Diäthylaminoäthoxy)-ä-methyl-5-          ally        l-benzoesäuremethylester    von 166 bis  <B>168'</B> als farblose     Flüssigkeit.    Das     daraus          mit    Salzsäure dargestellte     kristallisierte        Salz.     schmilzt nach dem     Umlö@sen    aus Aceton bei  <B>1</B>.11 bis 112'.  



  Der     neuen    Base kommt die folgende  Strukturformel zu:  
EMI0001.0058     




      Process for the preparation of a basic Plienoialkyläthers. The main patent describes a process for the preparation of a new basic phenol allzyl ether (2-. 6-Dim: ethoxy-4, -, allyl-phenyl diethyla-minoethyl ether).



  It now shows that a new phenol alkyl ether is obtained if 5-allyl .. o-cresotinic acid methyl ester (OH, CH, = <B> 2.3) </B> according to the process of the main patent with diethylaminoethyl chloride to 2- (c ) -Diethyl, aminoärtho @ xy) "- 8-merthyl-5-.aJ, lylbenzoic acid methyl ester.



  The product is said to be used as a cosmetic agent.



  <I> Example: </I> 75 parts by weight of 5-allyl-o-cresotinic acid methyester (OH, CH, = 2. ä) are combined with a dissolution of 8 parts by weight of sodium in 200 parts by weight of alcohol and 75 parts by weight of diethylaminoethyl - eh1oiid cooked for some time.

   After the alcohol has been removed and de-stilled, the residue is taken up in dilute hydrochloric acid, shaken out with ether and the ethereal aqueous solution is mixed with caustic soda until it has an alkaline reaction. The oil thus separated out is separated off, dried and distilled.



  Under 1 mm pressure, the 2- (co-diethylaminoethoxy) -a-methyl-5- allyl-benzoic acid methyl ester of 166 to 168 'obtained in this way boils as a colorless liquid. The crystallized salt prepared therefrom with hydrochloric acid. After dissolving from acetone, it melts at <B> 1 </B> .11 to 112 '.



  The new base has the following structural formula:
EMI0001.0058

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines basi schen Phenol,alkyläthers, dadurch gekenn zeichnet, dass man auf 5-Allyl-o-kresotin- säuremethylester (OH, CH3 = 2. 3) ein Di- äthylaminoäthylhalogenid zur Einwirkung bringt. PATENT CLAIM: Process for the preparation of a basic phenol, alkyl ether, characterized in that a diethylaminoethyl halide is brought into action on 5-allyl-o-cresotinic acid methyl ester (OH, CH3 = 2. 3). Der so erhailtene 2-(w-DiäthyLa,mino- äthoxy) -3-methyl-5-allyl- ben7,oesäuremethyl- ester ist eine farblose Flüssigkeit vom Siede- punkt 166-l68 unter 1 mm Druck, die mit Säuren neutrale Salze liefert. In pharmakologischer Beziehung verhält sich die neue Verbindung wie das Produkt des Hauptpatentes. The 2- (w-diethyLa, minoethoxy) -3-methyl-5-allylben7, methyl ester obtained in this way is a colorless liquid with a boiling point of 166-168 under 1 mm pressure which, with acids, gives neutral salts . From a pharmacological point of view, the new compound behaves like the product of the main patent. Sie soll als Lokalanästhe- tikum Verwendung finden. It should be used as a local anesthetic.
CH137144D 1927-04-11 1928-04-04 Process for the preparation of a basic phenol alkyl ether. CH137144A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE137144X 1927-04-11
CH135890T 1928-04-04

Publications (1)

Publication Number Publication Date
CH137144A true CH137144A (en) 1929-12-15

Family

ID=25712586

Family Applications (1)

Application Number Title Priority Date Filing Date
CH137144D CH137144A (en) 1927-04-11 1928-04-04 Process for the preparation of a basic phenol alkyl ether.

Country Status (1)

Country Link
CH (1) CH137144A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2914552A (en) * 1957-02-21 1959-11-24 Schenley Ind Inc 2-diloweralkylamino-alkoxy-3-methyl-benzoic acid esters

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2914552A (en) * 1957-02-21 1959-11-24 Schenley Ind Inc 2-diloweralkylamino-alkoxy-3-methyl-benzoic acid esters

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