CH150529A - Process for the preparation of a naphthalene derivative. - Google Patents

Process for the preparation of a naphthalene derivative.

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Publication number
CH150529A
CH150529A CH150529DA CH150529A CH 150529 A CH150529 A CH 150529A CH 150529D A CH150529D A CH 150529DA CH 150529 A CH150529 A CH 150529A
Authority
CH
Switzerland
Prior art keywords
naphthalene
preparation
chlorobenzyl
naphthalene derivative
aluminum chloride
Prior art date
Application number
Other languages
German (de)
Inventor
Aktiengesellsc Farbenindustrie
Original Assignee
Ig Farbenindustrie Ag
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 Ig Farbenindustrie Ag filed Critical Ig Farbenindustrie Ag
Publication of CH150529A publication Critical patent/CH150529A/en

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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

  

  Verfahren zur Darstellung eines     Naphtalinderivates.       In dem Hauptpatent ist ein Verfahren  zur Darstellung eines     Naphtalinderivates    be  schrieben, das dadurch gekennzeichnet ist,  dass man auf     1-Benzylnaphtalin        Benzoylchlo-          rid    in Gegenwart von Aluminiumchlorid ein  wirken lässt und das erhaltene Kondensations  produkt mit oxydierend wirkenden Mitteln  behandelt.  



  Es wurde nun gefunden, dass man in ganz  analoger Weise ein ebenfalls technisch wich  tiges     Naphtalinderivat    erhalten kann, wenn  man auf     4'-Chlorbenzyl-l-naphtalin        Benzoyl-          chlorid    in Gegenwart von Aluminiumchlorid  einwirken lässt und das erhaltene Kondensa  tionsprodukt mit oxydierend wirkenden Mitteln  behandelt.  



  Zweckmässig arbeitet man in Gegenwart  eines     indifferenten    organischen Verdünnungs  mittels.  



  Das Reaktionsprodukt, der Analyse und  dem Verfahren nach das noch nicht bekannte       1-(4'-Chlorbenzyl)-4-benzoylnaphtalin,    schmilzt    bei zirka 118   C, und kann zur Darstellung       wertvollergüpenfarbstoffeVerwendung    finden  <I>Beispiel:</I>  In eine auf     +    5   C abgekühlte Lösung  von 631 Teilen 4'-     Chlorbenzyl    -1-     naphtalin     und 386 Teilen     Benzoylchlorid    in 1560 Teilen  Benzol werden unter ständigem Rühren 400  Teile gemahlenes Aluminiumchlorid so einge  tragen, dass die Temperatur auf zirka 17 bis  20   C steigt. Unter     Salzsäureentwicklung     entsteht dabei eine gelbrote Lösung.

   Man  rührt noch 2-3 Stunden lang, trägt dann  in Wasser ein, trennt die     Benzollösung     ab und trocknet mit Soda. Zur Reinigung  wird das rohe Produkt zweckmässig im Va  kuum destilliert und die hochsiedende Haupt  fraktion aus Äther umkristallisiert. Das Reak  tionsprodukt bildet weisse Kristalle vom  Schmelzpunkt zirka 123   C. 18 Teile des  so erhaltenen Kondensationsproduktes werden  mit 150 Teilen Salpetersäure von 40<B>0</B> Bö      und 300 Teilen Wasser solange am     R.ück-          flusskühler    gekocht, bis die Entwicklung der  braunen     Stickoxyddämpfe    nachlässt. Dann  arbeitet man in der üblichen Weise auf.



  Process for the preparation of a naphthalene derivative. The main patent describes a process for the preparation of a naphthalene derivative which is characterized in that benzoyl chloride is allowed to act on 1-benzylnaphthalene in the presence of aluminum chloride and the condensation product obtained is treated with oxidizing agents.



  It has now been found that an equally technically important naphthalene derivative can be obtained in a very analogous manner if 4'-chlorobenzyl-1-naphthalene benzoyl chloride is allowed to act in the presence of aluminum chloride and the resulting condensation product is treated with oxidizing agents .



  It is expedient to work in the presence of an inert organic diluent.



  The reaction product, the analysis and the method according to the as yet unknown 1- (4'-chlorobenzyl) -4-benzoylnaphthalene, melts at about 118 C, and can be used to represent valuable mineral dyes <I> Example: </I> In a A solution of 631 parts of 4'-chlorobenzyl -1- naphthalene and 386 parts of benzoyl chloride in 1560 parts of benzene, cooled to + 5 ° C., 400 parts of ground aluminum chloride are added so that the temperature rises to about 17 to 20 ° C. with constant stirring. A yellow-red solution is formed with the evolution of hydrochloric acid.

   The mixture is stirred for another 2-3 hours, then poured into water, the benzene solution is separated off and dried with soda. For purification, the crude product is expediently distilled in vacuo and the high-boiling main fraction is recrystallized from ether. The reaction product forms white crystals with a melting point of about 123 C. 18 parts of the condensation product obtained in this way are boiled with 150 parts of nitric acid of 40 boiling point and 300 parts of water in a reflux condenser until development the brown nitrogen oxide vapors subsides. Then you work up in the usual way.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines Naphta- linderivates, dadurch gekennzeichnet, dass man auf 4'-Chlorbenzyl-l-naphtalin Benzoyl- chlorid in Gegenwart von Aluminiumchlorid einwirken lässt und das erhaltene Kondensa tionsprodukt mit oxydierend wirkenden Mitteln behandelt. Das Reaktionsprodukt, der Analyse und seinem Verhalten nach, das -noch nicht be- kannte 1-(4'-Chlorberizyl)-4-benzoylnaphtalin, schmilzt bei zirka<B>118'</B> C und kann zur Darstellung wertvoller Küpenfarbstoffe Ver wendung finden. PATENT CLAIM: Process for the preparation of a naphthalene derivative, characterized in that benzoyl chloride is allowed to act on 4'-chlorobenzyl-1-naphthalene in the presence of aluminum chloride and the condensation product obtained is treated with oxidizing agents. The reaction product, according to the analysis and its behavior, the -not yet known 1- (4'-chlorobericyl) -4-benzoylnaphthalene, melts at about 118 ° C and can be used to represent valuable vat dyes find application. UNTERANSPRUCH: Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man die Einwirkung des Benzoylchlorids auf das 4' - Chlorbenzyl -1- naphtalin in Gegenwart von Aluminiumchlo rid in einem indifferenten organischen Ver dünnungsmittel vornimmt. SUBSTANTIAL CLAIM: Process according to claim, characterized in that the action of the benzoyl chloride on the 4 '- chlorobenzyl -1- naphthalene in the presence of aluminum chloride in an inert organic diluent is carried out.
CH150529D 1929-04-05 1930-03-13 Process for the preparation of a naphthalene derivative. CH150529A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE150529X 1929-04-05
CH148753T 1930-03-13

Publications (1)

Publication Number Publication Date
CH150529A true CH150529A (en) 1931-10-31

Family

ID=25715248

Family Applications (1)

Application Number Title Priority Date Filing Date
CH150529D CH150529A (en) 1929-04-05 1930-03-13 Process for the preparation of a naphthalene derivative.

Country Status (1)

Country Link
CH (1) CH150529A (en)

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