DE561425C - Process for the preparation of 6-bromo-2-oxynaphthalene-3-carboxylic acid - Google Patents

Process for the preparation of 6-bromo-2-oxynaphthalene-3-carboxylic acid

Info

Publication number
DE561425C
DE561425C DE1930561425D DE561425DD DE561425C DE 561425 C DE561425 C DE 561425C DE 1930561425 D DE1930561425 D DE 1930561425D DE 561425D D DE561425D D DE 561425DD DE 561425 C DE561425 C DE 561425C
Authority
DE
Germany
Prior art keywords
oxynaphthalene
bromo
carboxylic acid
preparation
dibromo
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
DE1930561425D
Other languages
German (de)
Inventor
Dr Arthur Zitscher
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
Application granted granted Critical
Publication of DE561425C publication Critical patent/DE561425C/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 Herstellung von 6-Brom-2-oxynaphthalin-3-carbonsäure Gegenstand des Patents 549 840 ist ein Verfahren zur Herstellung von 6-Brom-2-oxynaphthalin-3-carbonsäure, welches darin besteht, daß man i, 6-Dibrom-2-oxynaphthalin-3-carbonsäure mit Alkalisulfiten auf Temperaturen über ioo' erhitzt.Process for the preparation of 6-bromo-2-oxynaphthalene-3-carboxylic acid The subject of patent 549 840 is a process for the preparation of 6-bromo-2-oxynaphthalene-3-carboxylic acid, which consists in that one i, 6-dibromo-2-oxynaphthalene-3-carboxylic acid with alkali sulfites heated to temperatures above 100 '.

Weitere Versuche haben nun gezeigt, daß die Abspaltung des Bromatoms in i-Stellung aus der i, 6-Dibrom-2-oxynaphthalin-3-carbonsäure nicht nur mit Alkalisulfiten, sondern auch durch Erhitzen in alkalischem Medium mit Traubenzucker mit guter Ausbeute gelingt. Beispiel i oo Gewichtsteile i, 6-Dibrom-2-oxynaphthalili-3-carbonsäure werden in 75o Raumteilen Wasser suspendiert und unter Zugabe von 125 Gewichtsteilen Traubenzucker zum Sieden erhitzt. Sodann läßt man i80 Raumteile 30%ige Natronlauge zulaufen, wobei das Gemisch mit roter Farbe in Lösung geht, und erhitzt noch etwa 8 Stunden unter Rückfluß zum Sieden. Durch Ansäuern des abgekühlten Reaktionsgemisches mit Salzsäure erhält man die 6-Brom-2-oxynaphthalin-3-carb,onsäure in einer Ausbeute von 95% der Theorie.Further experiments have now shown that the splitting off of the bromine atom in the i-position from the i, 6-dibromo-2-oxynaphthalene-3-carboxylic acid not only with alkali sulfites, but also by heating in an alkaline medium with glucose with good yield succeed. Example 100 parts by weight of 1,6-dibromo-2-oxynaphthalili-3-carboxylic acid are suspended in 75o parts by volume of water and with the addition of 125 parts by weight Dextrose heated to the boil. Then 180 parts by volume of 30% sodium hydroxide solution are left run in, whereby the mixture goes into solution with a red color, and still heats for about 8 hours under reflux to the boil. By acidifying the cooled reaction mixture with hydrochloric acid, the 6-bromo-2-oxynaphthalene-3-carb, onic acid is obtained in one yield of 95% of theory.

Claims (1)

PATENTANSPRUCH: Abänderung des durch Patent 549840 geschützten Verfahrens zur Herstellung von 6 - Brom- 2 -,oxynaphthalin- 3 -carb.onsäure, darin bestehend, daß man i, 6-Dibrom-2-oxynaphthalin-3-ca.rb,onsäure in alkalischem Medium mit Traubenzucker erhitzt.PATENT CLAIM: Modification of the process protected by patent 549840 for the production of 6 - bromo - 2 -, oxynaphthalene - 3 - carb.onic acid, consisting of that one i, 6-dibromo-2-oxynaphthalene-3-ca.rb, onic acid in an alkaline medium with grape sugar heated.
DE1930561425D 1930-12-16 1930-12-16 Process for the preparation of 6-bromo-2-oxynaphthalene-3-carboxylic acid Expired DE561425C (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE561425T 1930-12-16

Publications (1)

Publication Number Publication Date
DE561425C true DE561425C (en) 1932-10-14

Family

ID=6566229

Family Applications (1)

Application Number Title Priority Date Filing Date
DE1930561425D Expired DE561425C (en) 1930-12-16 1930-12-16 Process for the preparation of 6-bromo-2-oxynaphthalene-3-carboxylic acid

Country Status (1)

Country Link
DE (1) DE561425C (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2023186874A1 (en) 2022-03-28 2023-10-05 Huntsman Advanced Materials (Switzerland) Gmbh Disperse azo dyes based on 2-hydroxynaphthalene-3-carboxylic acid
WO2024170676A1 (en) 2023-02-17 2024-08-22 Archroma (Switzerland) Gmbh New class of disperse azo dyes, a process for the preparation thereof and the use thereof

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2023186874A1 (en) 2022-03-28 2023-10-05 Huntsman Advanced Materials (Switzerland) Gmbh Disperse azo dyes based on 2-hydroxynaphthalene-3-carboxylic acid
WO2024170676A1 (en) 2023-02-17 2024-08-22 Archroma (Switzerland) Gmbh New class of disperse azo dyes, a process for the preparation thereof and the use thereof

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