DE561629C - Process for the preparation of 1,6-dibromo-2-oxynaphthalene-3-carboxylic acid - Google Patents

Process for the preparation of 1,6-dibromo-2-oxynaphthalene-3-carboxylic acid

Info

Publication number
DE561629C
DE561629C DEI41456D DEI0041456D DE561629C DE 561629 C DE561629 C DE 561629C DE I41456 D DEI41456 D DE I41456D DE I0041456 D DEI0041456 D DE I0041456D DE 561629 C DE561629 C DE 561629C
Authority
DE
Germany
Prior art keywords
oxynaphthalene
carboxylic acid
dibromo
preparation
bromine
Prior art date
Legal status (The legal status 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 status listed.)
Expired
Application number
DEI41456D
Other languages
German (de)
Inventor
Dr Leopold Laska
Dr Johannes Wollemann
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
IG Farbenindustrie AG
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
Priority to DEI41456D priority Critical patent/DE561629C/en
Application granted granted Critical
Publication of DE561629C publication Critical patent/DE561629C/en
Expired legal-status Critical Current

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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 Darstellung von 1, 6-Dibrom-2-oxynaphthalin-3-carbonsäure Nach dem Verfahren des Patents 555 007 wird i, 6-Dibrom-2-oxynaphthalin-3-carbonsäure dadurch erhalten, daß man 2-Oxynaphthalin-3-carbons-#ii:re mit 2 Atomen Brom behandelt, wobei der gebildete Bromwasserstoff durch Schwefelsäureanhydrid zur Durchführung der Bromierung oxydiert wird.Process for the preparation of 1,6-dibromo-2-oxynaphthalene-3-carboxylic acid Following the procedure of patent 555 007, i, 6-dibromo-2-oxynaphthalene-3-carboxylic acid is obtained obtained by treating 2-oxynaphthalene-3-carbons- # ii: re with 2 atoms of bromine, the hydrogen bromide formed being carried out by sulfuric anhydride the bromination is oxidized.

Es wurde nun gefunden, daß man in diesem Verfahren die Verwendung von Schwefelsäureanhydrid vollständig vermeiden und mit gewöhnlicher Schwefelsäure zum gleichen Ziele gelangen kann, 'wenn man hierbei mit einem kleinen Überschuß von Brom arbeitet und die Reaktion durch Erhöhung der Temperatur zu Ende führt.It has now been found that this method can be used Avoid sulfuric anhydride completely and use ordinary sulfuric acid can achieve the same goal, 'if one is doing this with a small surplus of bromine works and completes the reaction by increasing the temperature.

Beispiel 75.2 Gewichtsteile 2-Oxynaphthalin-3-carbonsäurewerden in ,loo Gewichtsteile Schwefelsäure, 95o'oig, eingetragen. Unter Außenkühlung mit Kältemischung läßt man hierzu bei -- 5' 65 Gewichtsteile (statt 63,9 Gewichtsteile) Brom langsam in 2 Stunden zufließen und läßt dann allmählich die Temperatur auf Zimmertemperatur steigen. Nach etwa 2ostündigem Stehen wird die Temperatur in 6 Stunden bis auf 5o' gebracht und so lange gehalten, bis eine in Wasser gefällte Probe durch ihren Schmelzpunkt die Beendigung der Reaktion anzeigt. Die Reaktionsmasse wird dann in Wasser gegossen, filtriert und der Rückstand mit Wasser neutral gewaschen und getrocknet. Ausbeute 99.5 °`o der Theorie.Example 75.2 parts by weight of 2-oxynaphthalene-3-carboxylic acid are used in , loo parts by weight of sulfuric acid, 95o'oig, entered. Under external cooling with a cold mixture for this purpose, 65 parts by weight (instead of 63.9 parts by weight) of bromine are slowly left at -5 ' in 2 hours and then gradually leaves the temperature to room temperature rise. After standing for about 2 hours, the temperature will rise to 5o 'in 6 hours. brought and held until a sample precipitated in water through its melting point indicates the completion of the reaction. The reaction mass is then poured into water, filtered and the residue washed neutral with water and dried. yield 99.5 ° `o of theory.

Claims (1)

PATENTANSPRUCH: Abänderung des durch Patent 555 007 geschützten Verfahrens zur Darstellung von i.6-Dibrom-2-oxynaphthalin-3-carbonsäure aus 2-Oxynaphthalin-3-carbonsäure und 2 Atomen Brom, dadurch gekennzeichnet, daß. man an Stelle von Schwefelsäureanhydrid zur Oxydation des gebildeten Bromwasserstoffs hier gewöhnliche Schwefelsäure und einem kleinen I1berschuß von Brom verwendet und die Reaktion durch Erhöhung der Temperatur zu Ende führt.PATENT CLAIM: Modification of the process protected by patent 555 007 for the preparation of i.6-dibromo-2-oxynaphthalene-3-carboxylic acid from 2-oxynaphthalene-3-carboxylic acid and 2 atoms of bromine, characterized in that. instead of sulfuric anhydride to oxidize the hydrogen bromide formed, ordinary sulfuric acid and a small excess of bromine are used, and the reaction is brought to an end by increasing the temperature.
DEI41456D 1931-05-06 1931-05-06 Process for the preparation of 1,6-dibromo-2-oxynaphthalene-3-carboxylic acid Expired DE561629C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEI41456D DE561629C (en) 1931-05-06 1931-05-06 Process for the preparation of 1,6-dibromo-2-oxynaphthalene-3-carboxylic acid

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEI41456D DE561629C (en) 1931-05-06 1931-05-06 Process for the preparation of 1,6-dibromo-2-oxynaphthalene-3-carboxylic acid

Publications (1)

Publication Number Publication Date
DE561629C true DE561629C (en) 1932-10-15

Family

ID=7190548

Family Applications (1)

Application Number Title Priority Date Filing Date
DEI41456D Expired DE561629C (en) 1931-05-06 1931-05-06 Process for the preparation of 1,6-dibromo-2-oxynaphthalene-3-carboxylic acid

Country Status (1)

Country Link
DE (1) DE561629C (en)

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