CH135890A - 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
CH135890A
CH135890A CH135890DA CH135890A CH 135890 A CH135890 A CH 135890A CH 135890D A CH135890D A CH 135890DA CH 135890 A CH135890 A CH 135890A
Authority
CH
Switzerland
Prior art keywords
preparation
alkyl ether
basic
allyl
phenol
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 CH135890A publication Critical patent/CH135890A/en

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Description

  

  Verfahren zur Darstellung eines basischen     Phenolalkyläthers.       Die vorliegende Anmeldung     betrifft    ein  Verfahren zur Darstellung eines basischen       Phenolalkyläthers    mit     p-ständiger    ungesät  tigter Gruppe. Diesem Verfahren gemäss wird       2.6-Dimethoxy-4-allyl-phenol    mit einem     Di-          äthylaminoäthylhalogenid    behandelt.  



  Der so erhaltene     2.6-Dimethoxy-4-allyl-          phenyl-diäthylaminoäthyläther    stellt ein ba  sisch riechendes gelb gefärbtes Öl dar, das  mit Säuren neutrale Salze liefert. Die neue  Verbindung zeigt im pharmakologischen Ver  such eine starke Wirkung auf die glatte  Muskulatur. Dieses Verhalten ist überraschend,  weil zum Beispiel dem entsprechenden ba  sischen Äther des     Eugenols,    eine solche Wir  kung nicht zukommt. Das Produkt soll als  Lokalanästhetikum Verwendung finden.  



  <I>Beispiel:</I>  12 Gewichtsteile     4-Allyl-2,6-dimethoxy-l-          phenol    werden zusammen mit 12 Gewichts  teilen     Diäthylaminoäthylchlorid    in 50 Ge-         wichtsteilen    Alkohol gelöst und mit einer  Auflösung von 1,5 Gewichtsteilen Natrium  in 50 Gewichtsteile Alkohol versetzt. Darauf  wird einige Zeit erwärmt, der Alkohol ab  destilliert und der Rückstand mit Wasser  zersetzt. Es scheidet sich ein Öl ab, das ab  gehoben und     fraktionniert    wird.

   Unter einem  Druck von 5 mm geht der     Diäthylamino-          äthyläther    des     4-Allyl-2,6-dimethoxy-l-phe-          nols    als gelbgefärbtes Öl von 146     0-1511)     über. Er hat folgende Zusammensetzung  
EMI0001.0021     
    Das in diesem Beispiel verwendete     4-Allyl-          2,6-dimethoxy-l-phenol    wird nach der übli  chen Methode (A. 401,     S.50)    aus 2,6-Di-           methoxy-t-phenolallyläther    als gelbes Öl  erhalten.



  Process for the preparation of a basic phenol alkyl ether. The present application relates to a method for the preparation of a basic phenol alkyl ether with a p-position unsaturated group. According to this process, 2,6-dimethoxy-4-allyl-phenol is treated with a diethylaminoethyl halide.



  The 2,6-dimethoxy-4-allyl-phenyl-diethylaminoethyl ether obtained in this way is a yellow-colored oil with a basic smell which, with acids, gives neutral salts. In pharmacological tests, the new compound shows a strong effect on smooth muscles. This behavior is surprising because, for example, the corresponding basic ether of eugenol does not have such an effect. The product is intended to be used as a local anesthetic.



  <I> Example: </I> 12 parts by weight of 4-allyl-2,6-dimethoxy-1-phenol are dissolved together with 12 parts by weight of diethylaminoethyl chloride in 50 parts by weight of alcohol and 1.5 parts by weight of sodium are dissolved in 50 parts by weight Parts by weight of alcohol added. It is then heated for some time, the alcohol is distilled off and the residue is decomposed with water. An oil separates out, which is lifted off and fractionated.

   Under a pressure of 5 mm, the diethylaminoethyl ether of 4-allyl-2,6-dimethoxy-1-phenol passes over as a yellow oil from 146 0-1511). It has the following composition
EMI0001.0021
    The 4-allyl-2,6-dimethoxy-1-phenol used in this example is obtained as a yellow oil from 2,6-dimethoxy-t-phenol allyl ether by the usual method (A. 401, p.50).

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines basischen Phenolalkyläthers, dadurch gekennzeichnet, dass man auf 2.6-Dimethoxy-4-allyl-phenol Diäthylaminoäthylhalogenide zur Einwirkung bringt. Der so erhaltene 2.6-Dimethogy-4-allyl- phenyl-diäthylaminoäthyläther stellt ein ba- sisch riechendes gelb gefärbtes Öl dar, d mit Säuren neutrale Salze liefert. Die ne Verbindung zeigt im pharmakologischen VE such eine starke Wirkung auf die glat Muskulatur. Sie soll als Lokalanästhetiku Verwendung finden. PATENT CLAIM: Process for the preparation of a basic phenol alkyl ether, characterized in that diethylaminoethyl halides are brought into action on 2,6-dimethoxy-4-allyl-phenol. The 2,6-dimethogy-4-allyl-phenyl-diethylaminoethyl ether thus obtained is a basic-smelling yellow-colored oil which, with acids, yields neutral salts. The ne compound shows in pharmacological VE such a strong effect on the smooth muscles. It should be used as a local anesthetic.
CH135890D 1927-04-11 1928-04-04 Process for the preparation of a basic phenol alkyl ether. CH135890A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE135890X 1927-04-11

Publications (1)

Publication Number Publication Date
CH135890A true CH135890A (en) 1929-10-15

Family

ID=5666156

Family Applications (1)

Application Number Title Priority Date Filing Date
CH135890D CH135890A (en) 1927-04-11 1928-04-04 Process for the preparation of a basic phenol alkyl ether.

Country Status (1)

Country Link
CH (1) CH135890A (en)

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