CH276043A - Process for the preparation of cycloheptadecanone. - Google Patents

Process for the preparation of cycloheptadecanone.

Info

Publication number
CH276043A
CH276043A CH276043DA CH276043A CH 276043 A CH276043 A CH 276043A CH 276043D A CH276043D A CH 276043DA CH 276043 A CH276043 A CH 276043A
Authority
CH
Switzerland
Prior art keywords
cycloheptadecanone
preparation
hydrochloric acid
zinc
cycloheptadecanol
Prior art date
Application number
Other languages
French (fr)
Inventor
Firmenich Co Successeurs D Cie
Original Assignee
Firmenich & Co Successeurs De
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 Firmenich & Co Successeurs De filed Critical Firmenich & Co Successeurs De
Publication of CH276043A publication Critical patent/CH276043A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/65—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups

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

Description

  

  Procédé de préparation de la     cycloheptadécanone.       On a indiqué au brevet principal N  272568  que les     1,2-cyclanolones,    ayant de 10 à 18 chaî  nons dans le cycle, peuvent être partiellement  réduites, au moyen de zinc et d'acide chlor  hydrique, en     cyclanones    correspondantes, et  ledit brevet principal     porte    sur un procédé de  préparation de la     eyclopentadécanone.     



  Le présent brevet additionnel a pour  objet un procédé de préparation de la     cyclo-          heptadécanone.    Ce procédé est caractérisé en  ce que l'on soumet de la     cycloheptadécanol-1-          one-2    à une réduction partielle au moyen de  zinc et d'acide chlorhydrique.  



  Cette réduction peut être conduite en  l'absence ou en présence d'un     dissolvant    orga  nique, par exemple dans un milieu liquide  renfermant un tel dissolvant. La     cy        clohepta-          décanone    obtenue, qui est un composé connu,  peut avantageusement être utilisée comme ma  tière première dans l'industrie des parfums.  



  Voici, à titre d'exemple, comment le pro  cédé du présent brevet peut être exécuté en  pratique  15 g de     cycloheptadécanol-1-one-2    brute,  préparée à partir de 24 g de     heptadécane-          dioate-1,1.7    de méthyle sont dissous dans 38 g  d'acide acétique. Cette solution est ensuite  mélangée avec 35 g d'acide chlorhydrique       (-l00/0)    et. versée sur 20 g de laine de zinc.    La température est portée rapidement à<B>1000.</B>  On ajoute de l'acide chlorhydrique concentré  dès que l'ébullition devient moins intense.

    Quand 80     em3        d'HCl    sont introduits, on ajoute  encore une fois 20 g de laine de zinc et con-,       tinue    le chauffage en ajoutant encore 80 g  d'acide chlorhydrique et 40 g d'acide acétique  dans l'espace d'environ une     heure.    Le produit  de réaction est extrait à froid et, après dilu  tion à l'eau, au moyen d'éther de pétrole.  Après lavage à neutralité, on distille le pro  duit dans un bon vide. Point d'ébullition     corr.     1q5  C sous 0,3 mm de Hg, P.

   F. 630 C.     Rende-          ment        environ        70%.        Le        reste        est        composé     d'hydrocarbures (têtes) et de résines (queues).



  Process for the preparation of cycloheptadecanone. It was stated in main patent No. 272568 that 1,2-cyclanolones, having 10 to 18 ring members, can be partially reduced, by means of zinc and hydrochloric acid, to corresponding cyclanones, and said patent main focus is on a process for preparing eyclopentadecanone.



  The subject of the present additional patent is a process for the preparation of cycloheptadecanone. This process is characterized in that cycloheptadecanol-1-one-2 is subjected to partial reduction by means of zinc and hydrochloric acid.



  This reduction can be carried out in the absence or in the presence of an organic solvent, for example in a liquid medium containing such a solvent. The cy cloheptadecanone obtained, which is a known compound, can advantageously be used as a raw material in the perfume industry.



  Here is, by way of example, how the process of the present patent can be carried out in practice 15 g of crude cycloheptadecanol-1-one-2, prepared from 24 g of methyl heptadecanodioate-1,1.7 are dissolved in 38 g of acetic acid. This solution is then mixed with 35 g of hydrochloric acid (-l00 / 0) and. poured on 20 g of zinc wool. The temperature is quickly raised to <B> 1000. </B> Concentrated hydrochloric acid is added as soon as the boiling becomes less intense.

    When 80 em3 of HCl are introduced, another 20 g of zinc wool is added and the heating is continued by adding a further 80 g of hydrochloric acid and 40 g of acetic acid in the space of approximately one o'clock. The reaction product is extracted cold and, after dilution with water, with petroleum ether. After washing to neutrality, the product is distilled in a good vacuum. Boiling point corr. 1q5 C at 0.3 mm Hg, P.

   F. 630 C. Yield about 70%. The rest is made up of hydrocarbons (heads) and resins (tails).

Claims (1)

REVENDICATION: Procédé de préparation de la cyclohepta- décanone, caractérisé en ce que l'on soumet de la cycloheptadécanol-1-one-2 à une réduction partielle att moyen de zinc et d'acide chlor hydrique. SOUS-REVENDICATION Procédé selon la revendication, caractérisé en ce que l'on effectue la réduction partielle dans un milieu liquide renfermant un dissol vant organique. CLAIM: Process for preparing cycloheptadecanone, characterized in that cycloheptadecanol-1-one-2 is subjected to a partial reduction by means of zinc and hydrochloric acid. SUB-CLAIM Process according to claim, characterized in that the partial reduction is carried out in a liquid medium containing an organic solvent.
CH276043D 1947-10-07 1947-10-07 Process for the preparation of cycloheptadecanone. CH276043A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH276043T 1947-10-07
CH272568T 1947-10-07

Publications (1)

Publication Number Publication Date
CH276043A true CH276043A (en) 1951-06-15

Family

ID=25731366

Family Applications (1)

Application Number Title Priority Date Filing Date
CH276043D CH276043A (en) 1947-10-07 1947-10-07 Process for the preparation of cycloheptadecanone.

Country Status (1)

Country Link
CH (1) CH276043A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1032693B (en) * 1952-12-05 1958-06-19 Eastman Kodak Co Method and device for manufacturing filter elements for tobacco smoke

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1032693B (en) * 1952-12-05 1958-06-19 Eastman Kodak Co Method and device for manufacturing filter elements for tobacco smoke

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