CH96996A - Process for the preparation of a carbonyl derivative of α-naphthol. - Google Patents

Process for the preparation of a carbonyl derivative of α-naphthol.

Info

Publication number
CH96996A
CH96996A CH96996DA CH96996A CH 96996 A CH96996 A CH 96996A CH 96996D A CH96996D A CH 96996DA CH 96996 A CH96996 A CH 96996A
Authority
CH
Switzerland
Prior art keywords
naphthol
carboxylic acid
sodium hydroxide
hydroxide solution
naphtol
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 CH96996A publication Critical patent/CH96996A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C65/01—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups
    • C07C65/105—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups polycyclic
    • C07C65/11—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups polycyclic with carboxyl groups on a condensed ring system containing two rings

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

Description

  

  Verfahren zur Herstellung eines     Carbonylderivates    des     a-Naphtols.       mit warmer verdünnter     Sodalösung    durchge  rührt und nach dem Erkalten die Lösung  vom Rückstand abgegossen. Aus diesem lässt  sich durch     Ümlösen    aus Alkohol der     Äthyl-          ester    der     1-Naphtol-4-carbonsäure    isolieren,  während aus der     Sodalösung    durch Ansäuern  das     4.4'-Dioxy-1:

  l'-dynaphtylketon    abge  schieden wird, welches, aus Eisessig umge  löst, fast farblose Kristalle vom     Fp.    2430  bildet, die sich in     Sodalösung    und in Natron  lauge mit kräftig gelber Farbe lösen.  



  Der     Äthylester    der     1-Naphtol-4-carbon-          säure    bildet fast farblose, bei 1340 schmel  zende Kristalle, welche in Natronlauge und  verdünnter warmer     Sodalösung    leicht löslich  sind. Durch Verseifen mit heisser Natron  lauge wird die von Heller beschriebene     1-          Naphtol-4-carbonsäure    vom     Fp.    183-1840  (B. 45,675) erhalten.

      Es wurde gefunden, dass, wenn man auf       a-Naphtol    in Gegenwart von Äthylalkohol  und von säurebindenden Mitteln ein Tetra  halogenmethan einwirken lässt, man neben  dem Farbstoff des Patentes 90707 und an  deren Produkten, wie u. a. dem     4.4'-Dioxy-          1:1'-dinaphtylketon,    den     Äthylester    der     1-          Naphtol-4-carbonsäure    erhält, den man aus  der Reaktionsmasse auf Grund seiner Lös  lichkeit in organischen Lösungsmitteln, seiner       Unlöslichkeit    in Wasser und seines Verhaltens  gegen Säuren und Alkalien isoliert.  



  <I>Beispiel</I>  144 Teile     a-Naphtol    werden in 500     Tei-          len        Natronlauge        ä        40        %        Gew.        und        1200        Tei-          len    Äthylalkohol gelöst. Hierauf gibt man  154 Teile     Tetrachlorkohlenstoff    und 1 Teil  Kupferpulver hinzu und rührt das Ganze  einige Stunden, indem man durch Kühlen  sorgt, dass die Temperatur nicht über 500  steigt.

   Das tief blaugrüne Reaktionsgemisch  wird nun mit Mineralsäure neutralisiert, von  anorganischen Salzen     abfiltriert    und der Al  kohol     abdestilliert.    Der Rückstand wird dann



  Process for the preparation of a carbonyl derivative of α-naphthol. stirred with warm, dilute soda solution and poured off the residue after cooling. The ethyl ester of 1-naphthol-4-carboxylic acid can be isolated from this by dissolving it from alcohol, while the 4.4'-dioxy-1 is obtained from the soda solution by acidification:

  l'-dynaphtyl ketone is deposited, which, converted from glacial acetic acid, forms almost colorless crystals of melting point 2430, which dissolve in soda solution and in sodium hydroxide solution with a bright yellow color.



  The ethyl ester of 1-naphthol-4-carboxylic acid forms almost colorless crystals which melt at 1340 and which are easily soluble in sodium hydroxide solution and dilute warm soda solution. Saponification with hot sodium hydroxide solution gives the 1-naphthol-4-carboxylic acid, described by Heller, of melting point 183-1840 (B. 45.675).

      It has been found that if a tetra halomethane is allowed to act on a-naphtol in the presence of ethyl alcohol and acid-binding agents, in addition to the dye of patent 90707 and its products, such as u. a. 4.4'-Dioxy- 1: 1'-dinaphtyl ketone, the ethyl ester of 1-naphthol-4-carboxylic acid, which is obtained from the reaction mass due to its solubility in organic solvents, its insolubility in water and its behavior towards acids and alkalis isolated.



  <I> Example </I> 144 parts of a-naphtol are dissolved in 500 parts of 40% by weight sodium hydroxide solution and 1200 parts of ethyl alcohol. 154 parts of carbon tetrachloride and 1 part of copper powder are then added and the whole is stirred for a few hours by ensuring that the temperature does not rise above 500 by cooling.

   The deep blue-green reaction mixture is then neutralized with mineral acid, the inorganic salts are filtered off and the alcohol is distilled off. The residue will then

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines Carbonyl- derivates des a-Naphtols, dadurch gekenn zeichnet, dass man auf a-Naphtol in Gegen wart von Äthylalkohol und von säurebinden- den Mitteln ein Tetrahalogenmethan einwirken lässt und dass man den so entstandenen Äthyl- ester der 1-Naphtol-4-ca.rbonsäure aus der Reaktionsmasse auf Grund seiner Löslichkeit in organischen Lösungsmitteln, PATENT CLAIM: Process for the production of a carbonyl derivative of a-naphtol, characterized in that a tetrahalomethane is allowed to act on a-naphtol in the presence of ethyl alcohol and acid-binding agents and that the ethyl ester of 1 -Naphthol-4-carboxylic acid from the reaction mass due to its solubility in organic solvents, seiner Unlös- lichkeit in Wasser und seines Verhaltens gegen Säuren und Alkalien isoliert. Der Äthylester der 1-I\Taphtol-4-carbonsäiire bildet fast farb lose, bei 134 schmelzende Kristalle, welche in Natronlauge und verdünnter warmer Soda lösung leicht löslich sind. Durch Verseifen mit heisser Natronlauge wird die von Heller beschriebene 1-Naphtol-4-carbonsäure vom Fp. 183-184 (B. 45,675) erhalten. its insolubility in water and its behavior towards acids and alkalis. The ethyl ester of 1-taphtol-4-carboxylic acid forms almost colorless, melting crystals at 134, which are easily soluble in sodium hydroxide solution and dilute warm soda solution. Saponification with hot sodium hydroxide solution gives the 1-naphthol-4-carboxylic acid described by Heller with a melting point of 183-184 (B. 45,675).
CH96996D 1921-05-31 1921-05-31 Process for the preparation of a carbonyl derivative of α-naphthol. CH96996A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH96996T 1921-05-31
CH96665T 1921-05-31

Publications (1)

Publication Number Publication Date
CH96996A true CH96996A (en) 1922-11-16

Family

ID=25705126

Family Applications (1)

Application Number Title Priority Date Filing Date
CH96996D CH96996A (en) 1921-05-31 1921-05-31 Process for the preparation of a carbonyl derivative of α-naphthol.

Country Status (1)

Country Link
CH (1) CH96996A (en)

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