CH262555A - Process for the production of a-halo-y-lactones from a, y-dihalo-fatty acids. - Google Patents

Process for the production of a-halo-y-lactones from a, y-dihalo-fatty acids.

Info

Publication number
CH262555A
CH262555A CH262555DA CH262555A CH 262555 A CH262555 A CH 262555A CH 262555D A CH262555D A CH 262555DA CH 262555 A CH262555 A CH 262555A
Authority
CH
Switzerland
Prior art keywords
fatty acids
dihalo
lactones
halo
production
Prior art date
Application number
Other languages
German (de)
Inventor
Gustav Dr Bischoff
Original Assignee
Gustav Dr Bischoff
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 Gustav Dr Bischoff filed Critical Gustav Dr Bischoff
Publication of CH262555A publication Critical patent/CH262555A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/32—Oxygen atoms
    • C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form

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

Description

  

  Verfahren zur Herstellung von     a-Halogen-r-lactonen    aus     a,r-Dihalogen-fettsäuren.       Es ist bekannt, dass man aus     y-Halogen-          fettsäuren    durch Destillation im Vakuum  oder durch Neutralisation mit Alkali in der  Kälte zu den entsprechenden     y-Lactonen    ge  langen kann. Es ist ferner bekannt, dass man  aus     a,y-Dihalogen-fettsäuren    durch Destilla  tion im Vakuum unter Abspaltung von Halo  genwasserstoff     a-Halogen-y-lactone    herstellen  kann (J.     americ.        Soc.    67, 2218; 1946).

   Es  wurde nun gefunden, dass man die letztere  Umsetzung einfacher und mit besseren Aus  beuten dadurch ausführen kann, dass man die       a,y-Dihalogen-fettsäuren    in Gegenwart von  Wasser auf Temperaturen über 60  erhitzt.       Überraschenderweise    bleibt hierbei das     a-          Halogenatom    vollkommen     unangegriffen,     während das     y-ständige    Halogenatom in Form  von Halogenwasserstoff unter gleichzeitigem       Ringsehluss    abgespalten wird.

      <I>Beispiel:</I>  246 g     a,y-Dibrom-buttersäure,    in 200     cm3     Wasser suspendiert, werden 3 Stunden am       Rückfluss    gekocht. Nach dem Abkühlen haben  sich zwei Schichten gebildet, deren untere ab  getrennt wird, während die obere,     wässrige     Schicht mehrmals mit     Methylenchlorid    aus  geschüttelt wird. Die verschiedenen Anteile  des Reaktionsproduktes werden vereinigt; sie  hinterlassen nach dem     Abdestillieren    des Lö  sungsmittels 160 g     co4Brom-butyrolacton    vom  spezifischen Gewicht<B>d=1,830.</B>  



  Ausbeute.- 95     %.  



  Process for the preparation of a-halo-r-lactones from a, r-dihalo-fatty acids. It is known that y-halogen fatty acids can be obtained from y-halogen fatty acids by distillation in vacuo or by neutralization with alkali in the cold to give the corresponding y-lactones. It is also known that α-halo-γ-lactones can be prepared from α, γ-dihalo-fatty acids by distillation in vacuo with elimination of halogenated hydrogen (J. Americ. Soc. 67, 2218; 1946).

   It has now been found that the latter reaction can be carried out more easily and with better yields by heating the α, γ-dihalo-fatty acids to temperatures above 60 in the presence of water. Surprisingly, the a-halogen atom remains completely unaffected, while the y-halogen atom is split off in the form of hydrogen halide with simultaneous ring closure.

      <I> Example: </I> 246 g of a, γ-dibromobutyric acid, suspended in 200 cm3 of water, are refluxed for 3 hours. After cooling, two layers have formed, the lower of which is separated while the upper, aqueous layer is shaken out several times with methylene chloride. The various proportions of the reaction product are combined; After the solvent has been distilled off, they leave behind 160 g of co4-bromobutyrolactone with a specific weight of <B> d = 1.830. </B>



  Yield. - 95%.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von a-Halogen- y-lactonen durch Abspaltung von Halogenwas serstoff aus a,y-Dihalogen-fettsäuren, dadurch gekennzeichnet, dass man die a,y-Dihalogen- fettsäuren in Gegenwart von Wasser auf Temperaturen über 60 erhitzt. PATENT CLAIM: Process for the preparation of a-halo-y-lactones by splitting off hydrogen halide from a, y-dihalo-fatty acids, characterized in that the a, y-dihalo-fatty acids are heated to temperatures above 60 in the presence of water.
CH262555D 1948-01-21 1948-01-21 Process for the production of a-halo-y-lactones from a, y-dihalo-fatty acids. CH262555A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH262555T 1948-01-21

Publications (1)

Publication Number Publication Date
CH262555A true CH262555A (en) 1949-07-15

Family

ID=4474410

Family Applications (1)

Application Number Title Priority Date Filing Date
CH262555D CH262555A (en) 1948-01-21 1948-01-21 Process for the production of a-halo-y-lactones from a, y-dihalo-fatty acids.

Country Status (1)

Country Link
CH (1) CH262555A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2469409A1 (en) * 1979-11-13 1981-05-22 Chevron Res PROCESS FOR THE PREPARATION OF A LACTONE-ANILINE

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2469409A1 (en) * 1979-11-13 1981-05-22 Chevron Res PROCESS FOR THE PREPARATION OF A LACTONE-ANILINE

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