CH281750A - Process for preparing 2,5-diacetoxy-2,5-dihydrofuran. - Google Patents

Process for preparing 2,5-diacetoxy-2,5-dihydrofuran.

Info

Publication number
CH281750A
CH281750A CH281750DA CH281750A CH 281750 A CH281750 A CH 281750A CH 281750D A CH281750D A CH 281750DA CH 281750 A CH281750 A CH 281750A
Authority
CH
Switzerland
Prior art keywords
diacetoxy
preparing
dihydrofuran
agent
acetic acid
Prior art date
Application number
Other languages
French (fr)
Inventor
A S Kemisk Vaerk Koge
Original Assignee
Koege Kemisk Vaerk
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 Koege Kemisk Vaerk filed Critical Koege Kemisk Vaerk
Publication of CH281750A publication Critical patent/CH281750A/en

Links

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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Furan Compounds (AREA)

Description

  

  Procédé de préparation de     2,5-diacétoxy-2,5-dihydrofurane.       La présente invention concerne un procédé  de     préparation    de     2,5-diacétoxy        2,5-dihydro-          furane    ayant la formule:  
EMI0001.0006     
    Ce composé, qui est nouveau, peut être  hydrolysé en donnant l'aldéhyde maléique,    corps très actif; il constitue par     conséquent.     une matière première intéressante pour beau  coup de synthèses.  



  Selon l'invention, le     2,5-diacétoxy-2,5-di-          hydrofurane    est préparé en traitant du     fiuane     par un halogène et de l'acide acétique, en pré  sence d'un agent fixant l'acide     halogènhydri-          que    engendré; cet agent sera par exemple un  sel d'un acide organique.  



  La réaction peut s'expliquer ainsi  
EMI0001.0013     
    On obtient facilement le composé désiré et.  la plupart du temps avec (les rendements con  venables.  



  <I>Exemple:</I>  20 g d'acétate de potassium et 7,25     cm-          de        furane    sont dissous dans<B>100</B>     em3    d'acide  acétique (glacial). On ajoute peu à peu, en  15 minutes, 5     em3    de brome     dissous    dans  100     em3    d'acide acétique glacial à une tem  pérature d'environ 10 C. Il. se précipite du  bromure de potassium qu'on sépare par fil  tration. La. solution filtrée est. distillée dans le  vide.

   Le     composé    désiré est: une huile vis  queuse, incolore, qui cristallise partiellement  si on la tient. quelque temps à basse tempé  rature et bout à environ     l.30     sous une pres  sion de 10 mm de     mereure.    Rendement: 13 g,  correspondant à 70% du rendement théorique.



  Process for preparing 2,5-diacetoxy-2,5-dihydrofuran. The present invention relates to a process for preparing 2,5-diacetoxy 2,5-dihydro-furan having the formula:
EMI0001.0006
    This compound, which is new, can be hydrolyzed to give maleic aldehyde, a very active substance; it therefore constitutes. an interesting raw material for many syntheses.



  According to the invention, 2,5-diacetoxy-2,5-di-hydrofuran is prepared by treating fiuane with a halogen and acetic acid, in the presence of a binding agent for the hydrogen halide generated. ; this agent will for example be a salt of an organic acid.



  The reaction can be explained as follows
EMI0001.0013
    The desired compound is easily obtained and. most of the time with (suitable yields.



  <I> Example: </I> 20 g of potassium acetate and 7.25 cm- of furan are dissolved in <B> 100 </B> em3 of acetic acid (glacial). Gradually, over 15 minutes, 5 em3 of bromine dissolved in 100 em3 of glacial acetic acid are added at a temperature of about 10 C. II. potassium bromide precipitates which is separated by filtration. The filtered solution is. distilled in vacuum.

   The desired compound is: a viscous, colorless oil which partially crystallizes if held. for some time at low temperature and boils at about 1.30 at a pressure of 10 mm. Yield: 13 g, corresponding to 70% of the theoretical yield.

Claims (1)

REVENDICATION: Procédé pour la préparation de 2,5-di- acétoxy-2,5-dihy drofurane, caractérisé par le traitement de furane avec un halogène et de l'acide acétique, en présence d'un agent fixant l'acide halogènhydrique engendré. Le nouveau composé obtenu se présente sous forme d'une huile visqueuse incolore qui cristallise partiel lement lorsqu'elle est maintenue quelque temps à basse température; il bout à environ 130 C sous une pression de 10 mm. SOUS-REVENDICATION: Procédé suivant la. revendication, caracté risé en ce que ledit agent est un sel d'un acide organique. CLAIM: Process for the preparation of 2,5-di-acetoxy-2,5-dihy drofuran, characterized by the treatment of furan with halogen and acetic acid, in the presence of an agent fixing the hydrogen halide acid generated. . The new compound obtained is in the form of a colorless viscous oil which partially crystallizes when it is kept for some time at low temperature; it boils at about 130 ° C. under a pressure of 10 mm. SUB-CLAIM: Process according to. claim, characterized in that said agent is a salt of an organic acid.
CH281750D 1947-04-29 1948-04-28 Process for preparing 2,5-diacetoxy-2,5-dihydrofuran. CH281750A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
SE281750X 1947-04-29

Publications (1)

Publication Number Publication Date
CH281750A true CH281750A (en) 1952-03-31

Family

ID=20307035

Family Applications (1)

Application Number Title Priority Date Filing Date
CH281750D CH281750A (en) 1947-04-29 1948-04-28 Process for preparing 2,5-diacetoxy-2,5-dihydrofuran.

Country Status (1)

Country Link
CH (1) CH281750A (en)

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