CH105396A - Process for the preparation of an aryloxynaphthyl ketone. - Google Patents

Process for the preparation of an aryloxynaphthyl ketone.

Info

Publication number
CH105396A
CH105396A CH105396DA CH105396A CH 105396 A CH105396 A CH 105396A CH 105396D A CH105396D A CH 105396DA CH 105396 A CH105396 A CH 105396A
Authority
CH
Switzerland
Prior art keywords
ketone
aryloxynaphthyl
preparation
benzotrichloride
parts
Prior art date
Application number
Other languages
German (de)
Inventor
Gesellschaft Fuer Chemis Basel
Original Assignee
Chem Ind Basel
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 Chem Ind Basel filed Critical Chem Ind Basel
Publication of CH105396A publication Critical patent/CH105396A/en

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/82Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
    • C07C49/83Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups polycyclic
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/008Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with tri- or tetrahalomethyl compounds
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/82Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy 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

  

  Verfahren 'zur Herstellung eines     Aryloaynaphthylketons.       Es wurde gefunden, dass man ein     Aryl-          oxynaphthylketon    herstellen kann, wenn man  auf 1     Molekül        a-Naphthol,    mit oder ohne  Zusatz von Verdünnungsmitteln, aber unter  Ausschluss von Alkalien, mindestens 1 Mole  kül     Benzotrichlorid    einwirken lässt. Das so  erhaltene     1-Phenylketon-4-oxyiaphthalin    ist  identisch mit dem     4-Oxynaphthalin-l-phenyl-          keton    des Patentes Nr. 99520.  



  <I>Beispiel Z:</I>  28,8 Teile     a-Naphthol    werden unter gutem  Kühlen und Rühren in 180 Teile konzen  trierte Schwefelsäure eingetragen und hierauf,  innerhalb 4     Stuciden,    mit 39 Teilen     Benzo-          trichlorid    versetzt. Nachdem alles     Benzotri-          chlorid    verschwunden ist, wird die grünliche  Reaktionsmasse auf Eis ausgetragen. Der  ausfallende Niederschlag wird filtriert, mit       Sodalösung    ausgekocht und die filtrierte  Lösung     ausgesäuert.    Das ausfallende rohe       1-Phenylketon-4-oxynaphthalin    kann zur Rei  nigung aus Benzol umgelöst werden.

      <I>Beispiel 2</I>  28,8 Teile     a-Naphthol    werden in 220 Tei  len Nitrobenzol gelöst und hierauf zuerst mit  10 Teilen Zinkoxyd und dann nach und nach,  im Laufe von 4 Stunden, mit 39 Teilen       Benzotrichlorid    versetzt. Wenn die Salzsäure  bildung nachgelassen hat, wird die Reaktions  masse mit     Sodalösung    versetzt, das     Nitro-          benzol    mit Wasserdampf abgeblasen, der       Destillationsrückstand    heiss filtriert,     ausge-          säuert.    Das ausgefallene     Rohketon    kann aus  Benzol umgelöst werden.  



  Statt Zinkoxyd können andere Oxyde und  Salze     bezw.    Metalle, sowie auch     Metalloide,     deren Oxyde,     Halogenide    und     Oxyhalogenide     verwendet werden.



  Process for the production of an aryloaynaphthyl ketone. It has been found that an aryl oxynaphthyl ketone can be produced if at least 1 mol of benzotrichloride is allowed to act on 1 molecule of a-naphthol, with or without the addition of diluents, but with the exclusion of alkalis. The 1-phenylketone-4-oxyiaphthalene obtained in this way is identical to the 4-oxynaphthalene-1-phenyl ketone of patent no. 99520.



  <I> Example Z: </I> 28.8 parts of a-naphthol are introduced into 180 parts of concentrated sulfuric acid with thorough cooling and stirring, and 39 parts of benzotrichloride are then added within 4 stucides. After all of the benzotrchloride has disappeared, the greenish reaction mass is poured onto ice. The resulting precipitate is filtered, boiled with soda solution and the filtered solution is acidified. The precipitating crude 1-phenylketone-4-oxynaphthalene can be redissolved from benzene for cleaning.

      <I> Example 2 </I> 28.8 parts of a-naphthol are dissolved in 220 parts of nitrobenzene and then initially 10 parts of zinc oxide and then gradually, over the course of 4 hours, 39 parts of benzotrichloride are added. When the formation of hydrochloric acid has subsided, soda solution is added to the reaction mixture, the nitrobenzene is blown off with steam, and the distillation residue is filtered hot and acidified. The precipitated crude ketone can be converted from benzene.



  Instead of zinc oxide, other oxides and salts can bezw. Metals, as well as metalloids, whose oxides, halides and oxyhalides are used.

 

Claims (1)

PATENTANTSPRUCI3 Verfahren zur Herstellung eines Aryloxy- naphthylketons des 1-Phenylketon-4-oxynaph- thalins, dadurch gekennzeichnet, dass man auf 1 Molekül a-Naphthol, unter Ausschluss von Alkalien, mindestens 1 Molekül Benzo- trichlorid einwirken lässt. UNTRRANSPRüCHR 1. Verfahren gemäss Patentanspruch, dadurch gekennzeichnet, dass man Benzotrichlorid mit Zusatz von Verdünnungsmitteln ein wirken lässt. 2. PATENTANTSPRUCI3 Process for the production of an aryloxynaphthyl ketone of 1-phenylketone-4-oxynaphthalene, characterized in that at least 1 molecule of benzotrichloride is allowed to act on 1 molecule of a-naphthol, with the exclusion of alkalis. UNTRRANSPRüCHR 1. Process according to claim, characterized in that benzotrichloride is allowed to act with the addition of diluents. 2. Verfahren gemäss Patentanspruch, dadurch gekennzeichnet, dass man Benzotrichlorid mit Zusatz von Kondensationsmitteln ein wirken lässt. Process according to claim, characterized in that benzotrichloride is allowed to act with the addition of condensing agents.
CH105396D 1921-09-24 1923-03-06 Process for the preparation of an aryloxynaphthyl ketone. CH105396A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH98559T 1921-09-24
CH105396T 1923-03-06

Publications (1)

Publication Number Publication Date
CH105396A true CH105396A (en) 1924-06-16

Family

ID=25705434

Family Applications (1)

Application Number Title Priority Date Filing Date
CH105396D CH105396A (en) 1921-09-24 1923-03-06 Process for the preparation of an aryloxynaphthyl ketone.

Country Status (1)

Country Link
CH (1) CH105396A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1092927B (en) * 1958-05-20 1960-11-17 Hoechst Ag Process for the preparation of 4,6-diacyl-1,3-dioxybenzenes

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1092927B (en) * 1958-05-20 1960-11-17 Hoechst Ag Process for the preparation of 4,6-diacyl-1,3-dioxybenzenes

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