CH482666A - New process for preparing pyrocine - Google Patents

New process for preparing pyrocine

Info

Publication number
CH482666A
CH482666A CH908569A CH908569A CH482666A CH 482666 A CH482666 A CH 482666A CH 908569 A CH908569 A CH 908569A CH 908569 A CH908569 A CH 908569A CH 482666 A CH482666 A CH 482666A
Authority
CH
Switzerland
Prior art keywords
pyrocine
preparing
new process
diacid
formula
Prior art date
Application number
CH908569A
Other languages
French (fr)
Inventor
Julia Marc
Original Assignee
Rhone Poulenc Sa
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
Priority claimed from FR79723A external-priority patent/FR1506425A/en
Priority claimed from FR96478A external-priority patent/FR92123E/en
Application filed by Rhone Poulenc Sa filed Critical Rhone Poulenc Sa
Publication of CH482666A publication Critical patent/CH482666A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D315/00—Heterocyclic compounds containing rings having one oxygen atom as the only ring hetero atom according to more than one of groups C07D303/00 - C07D313/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/14—Sulfones; Sulfoxides having sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/08—Preparation of carboxylic acids or their salts, halides or anhydrides from nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/377—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
    • C07C51/38—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups by decarboxylation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
    • C07C57/13—Dicarboxylic acids

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Description

  

  Nouveau procédé de préparation de la pyrocine    On sait d'après le brevet français No 1269127 que la  pyrocine, qui est la lactone de formule  
EMI0001.0000     
    peut constituer un intermédiaire dans la préparation de  l'acide chrysanthémique et qu'on peut la préparer par  action d'un ester bromacétique sur la méthyl-2 hexène-2  one-5.  



  On a maintenant trouvé que la pyrocine peut être  préparé par décarboxylation et cyclisation du diacide de  formule  
EMI0001.0001     
    Ce passage de (II) à (I), qui se fait avec un change  ment de squelette     carboné    dont on ne connaît pas de  précédent, est réalisé par chauffage à une température  d'au moins 1600 C.  



  Par exemple, par chauffage à l80  C sous pression  réduite (environ 10 mm de mercure) le diacide (II) est  transformé en lactone (I) qui distille. Le distillat cris  tallise     (fusion    51-53 C).     Le    rendement     peut    atteindre  87 % sur le diacide     précédent.     



  Le diacide de formule (II), qui est l'acide carboxy-2  triméthyl-4,4,6 heptadiène-2,5 oïque fondant à 151  1530 C, est un produit nouveau. Il peut être obtenu par  le     procédé    décrit dans le brevet suisse No 478079.



  New process for the preparation of pyrocine It is known from French patent No. 1269127 that pyrocine, which is the lactone of formula
EMI0001.0000
    can constitute an intermediate in the preparation of chrysanthemic acid and can be prepared by the action of a bromacetic ester on 2-methylhexene-2 one-5.



  It has now been found that pyrocine can be prepared by decarboxylation and cyclization of the diacid of formula
EMI0001.0001
    This passage from (II) to (I), which takes place with a change of carbon skeleton of which no precedent is known, is carried out by heating to a temperature of at least 1600 C.



  For example, by heating at 180 ° C. under reduced pressure (about 10 mm of mercury) the diacid (II) is converted into lactone (I) which distils. The distillate cris tallises (melting 51-53 C). The yield can reach 87% on the previous diacid.



  The diacid of formula (II), which is 2-carboxy-trimethyl-4,4,6 heptadiene-2,5 oic acid, melting point at 151 1530 C, is a new product. It can be obtained by the process described in Swiss Patent No. 478079.

Claims (1)

REVENDICATION Procédé de préparation de la pyrocine, caractérisé en ce que l'on chauffe un composé de formule EMI0001.0009 à une température au moins égale à 160() C. CLAIM Process for the preparation of pyrocine, characterized in that a compound of formula is heated EMI0001.0009 at a temperature of at least 160 () C.
CH908569A 1966-10-12 1969-10-11 New process for preparing pyrocine CH482666A (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
FR79723A FR1506425A (en) 1966-10-12 1966-10-12 New process for preparing chrysanthemic acid
FR96478A FR92123E (en) 1966-10-12 1967-02-24 New process for preparing chrysanthemic acid
FR96477A FR1519895A (en) 1966-10-12 1967-02-24 New process for preparing pyrocine
CH1416867A CH478079A (en) 1966-10-12 1967-10-11 Process for the preparation of a novel unsaturated dicarboxylic acid convertible into pyrocine

Publications (1)

Publication Number Publication Date
CH482666A true CH482666A (en) 1969-12-15

Family

ID=27429542

Family Applications (1)

Application Number Title Priority Date Filing Date
CH908569A CH482666A (en) 1966-10-12 1969-10-11 New process for preparing pyrocine

Country Status (1)

Country Link
CH (1) CH482666A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994007837A1 (en) * 1992-09-30 1994-04-14 Unichema Chemie B.V. Unsaturated aliphatic dicarboxylic acids

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994007837A1 (en) * 1992-09-30 1994-04-14 Unichema Chemie B.V. Unsaturated aliphatic dicarboxylic acids
US5753704A (en) * 1992-09-30 1998-05-19 Unichema Chemie B.V. Therapeutic compositions comprising unsaturated dioic acids or derivatives thereof

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