CH137676A - 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
CH137676A
CH137676A CH137676DA CH137676A CH 137676 A CH137676 A CH 137676A CH 137676D A CH137676D A CH 137676DA CH 137676 A CH137676 A CH 137676A
Authority
CH
Switzerland
Prior art keywords
preparation
alkyl ether
crotyl
phenol alkyl
basic 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 CH137676A publication Critical patent/CH137676A/en

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Description

  

  Verfahren zur Darstellung eines basischen     Phenolalkyläthers.       In dem Patent     Nr.137143    ist ein Verfahren  zur Darstellung eines basischen     Phenolalkyl-          äthers,    des     2-(co-Diäthylaminoäthoxy)-3-me-          thoxy    - 5 -     crotyl    -     benzoesäuremethylesters,    be  schrieben worden.  



  Es wurde nun gefunden, dass man zu  dem gleichen Produkt auch in der Weise  gelangen kann, wenn man     5-Crotyl-guajacol-          carbonsäuremethylester    (OH, OCHS = 2,3)  zunächst mit einem     Äthylendihalogenid    be  handelt und das dabei gewonnene     halogen-          haltige    Zwischenprodukt mit     Diäthylamin    zu  dem     2-(m-Diäthylaminoäthoxy)-3-metboxy-5-          crotyl-benzoesäuremethylester    umsetzt.  



       Beispiel:     20 Gewichtsteile der     Natriumverbindung     des     5-Crotyl-guajacolcarbocisäuremethylesters     (OH,     OCHS    = 2,3) werden zusammen mit  100 Gewichtsteilen     Äthylenbromid    einige Zeit  erhitzt. Nach erfolgter Umsetzung wird das  überschüssige     Äthylenbromid        abdestilliert    und  der Rückstand fraktioniert. Der dabei erhal  tene     Bromäthyläther    des     5-Crotyl-guajacol-          carbonsäuremethylesters    wird als fast farblose  Flüssigkeit erhalten.

      50 Gewichtsteile des so dargestellten       Bromäthyläthers    werden zusammen mit 50  Gewichtsteilen     Diäthylamin    unter Druck er  hitzt. Nach erfolgter Umsetzung wird mit  Wasser aufgenommen,     ausgeäthert    und die       ausgeätherte    Flüssigkeit alkalisch gemacht,  das sich abscheidende Öl     abgtrennt,    getrocknet  und destilliert. Unter 2 mm Druck siedet  der so erhaltene     2-(co-Diäthylaminoäthoxy)-3-          methoxy-5-crotyl-benzoesäuremethylester    von       200-202"    als gelb gefärbtes<B>01.</B>



  Process for the preparation of a basic phenol alkyl ether. In the patent No. 137143 a process for the preparation of a basic phenol alkyl ether, 2- (co-diethylaminoethoxy) -3-methoxy-5-crotyl-benzoic acid methyl ester, has been described.



  It has now been found that the same product can also be obtained if methyl 5-crotyl-guaiacol carboxylate (OH, OCHS = 2.3) is first treated with an ethylene dihalide and the halogen-containing intermediate product obtained in this way with diethylamine to form the 2- (m-diethylaminoethoxy) -3-metboxy-5-crotyl-benzoic acid methyl ester.



       Example: 20 parts by weight of the sodium compound of 5-crotyl-guaiacolcarbocic acid methyl ester (OH, OCHS = 2.3) are heated for some time together with 100 parts by weight of ethylene bromide. After the reaction has taken place, the excess ethylene bromide is distilled off and the residue is fractionated. The bromoethyl ether of 5-crotyl-guaiacol carboxylic acid methyl ester obtained in this way is obtained as an almost colorless liquid.

      50 parts by weight of the bromoethyl ether thus represented are heated together with 50 parts by weight of diethylamine under pressure. After the reaction has taken place, the mixture is taken up with water, extracted with ether and the extracted liquid is made alkaline, the oil which separates out is separated off, dried and distilled. The 2- (co-diethylaminoethoxy) -3-methoxy-5-crotyl-benzoic acid methyl ester of 200-202 "thus obtained boils under 2 mm pressure as a yellow-colored <B> 01. </B>

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines basischen Phenolalkyläthers, dadurch gekennzeichnet, dass man auf 5-Crotyl-guajacolcarbonsäure- methylester (OH, OCHS = 2,3) Äthylen- dihalogenid einwirken lässt und das gebildete halogenhaltige Zwischenprodukt mit Diäthyl- amin zum 2-(m-Diäthylaminoäthoxy)-3-me- thoxy-5. crotyl- benzoesäuremethylester um setzt. PATENT CLAIM: Process for the preparation of a basic phenol alkyl ether, characterized in that methyl 5-crotyl-guaiacolcarboxylate (OH, OCHS = 2,3) is allowed to act on ethylene dihalide and the halogen-containing intermediate formed is mixed with diethylamine to give 2- (m Diethylaminoethoxy) -3-methoxy-5. crotyl benzoic acid methyl ester sets.
CH137676D 1928-04-04 1928-04-04 Process for the preparation of a basic phenol alkyl ether. CH137676A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH136186T 1928-04-04
DE137676X 1929-04-11

Publications (1)

Publication Number Publication Date
CH137676A true CH137676A (en) 1930-01-15

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ID=25712654

Family Applications (1)

Application Number Title Priority Date Filing Date
CH137676D CH137676A (en) 1928-04-04 1928-04-04 Process for the preparation of a basic phenol alkyl ether.

Country Status (1)

Country Link
CH (1) CH137676A (en)

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