CH267953A - Process for the preparation of a compound related to vitamin A. - Google Patents

Process for the preparation of a compound related to vitamin A.

Info

Publication number
CH267953A
CH267953A CH267953DA CH267953A CH 267953 A CH267953 A CH 267953A CH 267953D A CH267953D A CH 267953DA CH 267953 A CH267953 A CH 267953A
Authority
CH
Switzerland
Prior art keywords
vitamin
preparation
ethyl
ketone
compound related
Prior art date
Application number
Other languages
German (de)
Inventor
N V Organon
Original Assignee
Organon Nv
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 Organon Nv filed Critical Organon Nv
Publication of CH267953A publication Critical patent/CH267953A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
    • C07C403/06—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by singly-bound oxygen atoms
    • C07C403/08—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by singly-bound oxygen atoms by hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

Landscapes

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

Description

  

      Verfahren   <B>zur Herstellung einer mit dem Vitamin A verwandten Verbindung.</B>    lm Schweizer Patent.     Nr.260994    ist ein       Verfahren    zur     Herstellung    der     Vit.amin-A-          Säure,    ausgehend vom     C,-Keton    und einer         organometallischen    Verbindung, beschrieben.

    Dem     C"        Keton    kommt. die Formel zu:  
EMI0001.0011     
    Gegenstand des vorliegenden Patentes ist  nun ein Verfahren zur Herstellung eines Kon  densationsproduktes des C"$     Ketons,    welches  dadurch gekennzeichnet ist, dass das genannte       Keton    mit einer     Äthylmetaliverbindung     umgesetzt und das Umsetzungsprodukt     hy        dro-          lytisch    zerlegt wird.  



  Als     Äthy        lmetallv        erbindung    kann beispiels  weise     Äthy        lmagnesiumbromid    oder Äthyl  lithium verwendet werden.  



  Das Endprodukt ist ein öl, das bei einem  Druck von 10-3 mm     Hg    zwischen 160 und  170  C überdestilliert. Es ist ein wichtiges  Zwischenprodukt für die Synthese von Vit  amin A.  



  <I>Beispiel:</I>  Eine Lösung von 25,8 g     C,$-Keton    wird  unter Eiskühlung unter fortgesetztem Rüh  ren tropfenweise einer Lösung von     Äthyl-          lithium    zugesetzt, welche ihrerseits aus 2 g         Lithium,    16     g        Äthy        ljodid    und 25     ein'    Benzol  hergestellt wurde.

   Nach Zersetzung des Reak  tionsgemisches mit Eiswasser, Extraktion mit       :lther    und Destillation im     Hochvakuum    wird  ein öl erhalten, welches bei einem     Druck    von  10-3 mm     Hg    zwischen 160 und 170  C über  destilliert.  



  Dasselbe Produkt. wird erhalten, wenn als       organometallische    Verbindung     Äthylmagne-          siumbromid    statt.     Äthy        llithium    verwendet  wird. Als Nebenreaktion findet aber bisweilen  auch Addition an     auseinanderliegenden    Dop  pelbindungen statt     (1,4-Ad(lition).    Die Tren  nung der verschiedenen Produkte gelingt dann  nur mit Hilfe einer zeitraubenden     Chromato-          graphierung.  



      Process <B> for the production of a compound related to vitamin A. </B> In the Swiss patent. No. 260994 describes a process for the production of vitamin A acid, starting from the C, ketone and an organometallic compound.

    The formula corresponds to the C "ketone:
EMI0001.0011
    The subject of the present patent is a process for the production of a condensation product of the C "$ ketone, which is characterized in that said ketone is reacted with an ethyl metal compound and the reaction product is hydrolyzed.



  Ethy lmagnesium bromide or ethyl lithium, for example, can be used as an ethylene metal compound.



  The end product is an oil that distills over between 160 and 170 C at a pressure of 10-3 mm Hg. It is an important intermediate for the synthesis of vitamin A.



  <I> Example: </I> A solution of 25.8 g of C, $ ketone is added dropwise to a solution of ethyl lithium, which in turn consists of 2 g of lithium, 16 g of ethyl iodide and 25 a 'benzene was produced.

   After decomposition of the reaction mixture with ice water, extraction with: ether and distillation in a high vacuum, an oil is obtained which distills over at a pressure of 10-3 mm Hg between 160 and 170 ° C.



  Same product. is obtained when ethylmagnesium bromide is used as the organometallic compound. Ethy llithium is used. As a side reaction, however, addition of double bonds that are located apart takes place (1,4-addition). The different products can then only be separated with the help of time-consuming chromatography.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines Konden sationsproduktes, eines bei einem Druck von 10-3 mm Hg zwischen 160 und 170 C über- destillierenden Öls, dadurch gekennzeichnet, dass das Keton der Formel EMI0002.0002 mit. einer Äthylmetallv erbindung umgesetzt und das Umsetzungsprodukt hydrolytisch zer legt wird. UNTERANSPRÜCHE: 1. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass als Äthylmetall- verbindung Äthyllithium verwendet wird. 2. PATENT CLAIM: Process for the production of a condensation product, an oil which distills over at a pressure of 10-3 mm Hg between 160 and 170 C, characterized in that the ketone of the formula EMI0002.0002 With. an ethyl metal compound implemented and the reaction product is hydrolytically decomposed. SUBClaims: 1. Method according to patent claim, characterized in that ethyl lithium is used as the ethyl metal compound. 2. Verfahren nach Patentanspi-ticli, da durch gekennzeichnet, dass als Ä tliyImetal.l- verbindung Ätliylmagliesiumbromid verwen det wird. The method according to patent application, characterized in that the ÄtliyImetal.l- connection is Ätliylmagliesiumbromid used.
CH267953D 1944-06-15 1946-09-06 Process for the preparation of a compound related to vitamin A. CH267953A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
NL267953X 1944-06-15

Publications (1)

Publication Number Publication Date
CH267953A true CH267953A (en) 1950-04-30

Family

ID=19781813

Family Applications (1)

Application Number Title Priority Date Filing Date
CH267953D CH267953A (en) 1944-06-15 1946-09-06 Process for the preparation of a compound related to vitamin A.

Country Status (1)

Country Link
CH (1) CH267953A (en)

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