CH139367A - Process for the preparation of 4- (oxyethyl) -amino-1-oxybenzene-2-carboxylic acid. - Google Patents

Process for the preparation of 4- (oxyethyl) -amino-1-oxybenzene-2-carboxylic acid.

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Publication number
CH139367A
CH139367A CH139367DA CH139367A CH 139367 A CH139367 A CH 139367A CH 139367D A CH139367D A CH 139367DA CH 139367 A CH139367 A CH 139367A
Authority
CH
Switzerland
Prior art keywords
carboxylic acid
amino
oxybenzene
preparation
oxyethyl
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 CH139367A publication Critical patent/CH139367A/en

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

Description

  

  Verfahren zur Darstellung von     4-(Oxyäthyl)-amino-l-oxybenzol-2-earbonsäure.       Wie gefunden wurde, erhält man     4-(Oxy-          äthyl)-amino-l-oxyberrzol-2-carbonsäure,    wenn  man 1     Mol        4-Amirro-l-oxybenzol-2-carbonsäure     mit 1     Mol    eines     Halogenhydrins    des Glykols  kondensiert.  



  Die neue Verbindung bildet farblose, bei  206   C sich zersetzende Kristalle. Sie ist  wenig löslich irr kaltem Wasser oder Alkohol,  leichter in heissem Wasser. Sie löst sich  leicht in Säuren und     Ätzalkalien.    Sie kann  unter anderem als photographischer Entwickler  Verwendung finden.  



       Beispiel:     153 Teile     4-Amino-l-oxybenzol-2..carbon-          säure    werden mit 165 Teilen     Natriumcarbonat     und 1500 Teilen Wasser auf<B>800</B> C erhitzt  und unter Rühren auf einmal mit 120 Teilen       Äthylenchlorhydrin    versetzt. Man erhitzt  langsam zum Sieden und kocht am Rück  flusskühler bis zu der nach einigen Stunden  beendeten Umsetzung. Man neutralisiert mit    verdünnter Salzsäure, filtriert und befreit das  Filtrat im Vakuum vom Wasser.

   Den Rück  stand zieht man mehrmals mit verdünntem  Alkohol aus und gewinnt daraus die     4-(Oxy-          äthyl)-arrrino-l-oxybenzol-2-carbonsäurein    fast  farblosen Kristallen, die nach     Umkriställisieren     aus heissem Wasser oder verdünntem Alkohol  rein sind.



  Process for the preparation of 4- (oxyethyl) -amino-1-oxybenzene-2-carboxylic acid. It has been found that 4- (oxyethyl) -amino-1-oxyberrzene-2-carboxylic acid is obtained if 1 mole of 4-amirro-1-oxybenzene-2-carboxylic acid is condensed with 1 mole of a glycol halohydrin.



  The new compound forms colorless crystals that decompose at 206 ° C. It is not very soluble in cold water or alcohol, more easily in hot water. It dissolves easily in acids and caustic alkalis. It can be used, among other things, as a photographic developer.



       Example: 153 parts of 4-amino-1-oxybenzene-2-carboxylic acid are heated with 165 parts of sodium carbonate and 1500 parts of water to 800 C and 120 parts of ethylene chlorohydrin are added all at once while stirring. The mixture is slowly heated to the boil and refluxed until the reaction has ended after a few hours. It is neutralized with dilute hydrochloric acid, filtered and the filtrate is freed from water in vacuo.

   The residue is extracted several times with dilute alcohol and the 4- (oxyethyl) -arrrino-1-oxybenzene-2-carboxylic acid is obtained in almost colorless crystals, which are pure after recrystallization from hot water or dilute alcohol.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung von 4-(Oxy- äthyl) - amino -1-oxyberrzol-2-carbonsäur e, da durch gekennzeichnet, dass man 1 Mol 4- Arnino-l-oxybenzol-2-carbonsäure mit 1 Mol eines Halogenhydrins des Glykols kondensiert. Die neue Verbindung bildet farblose, bei <B>2060</B> C sich zersetzende Kristalle. Sie ist leicht löslich in Säuren und Ätzalkalien, wenig löslich in Wasser oder Alkohol, leichter in heissem Wasser. PATENT CLAIM: Process for the preparation of 4- (oxy-ethyl) - amino -1-oxyberrzene-2-carboxylic acid e, characterized in that 1 mole of 4-amino-1-oxybenzene-2-carboxylic acid is mixed with 1 mole of a halohydrin des Glycol condenses. The new compound forms colorless crystals that decompose at <B> 2060 </B> C. It is easily soluble in acids and caustic alkalis, slightly soluble in water or alcohol, more easily in hot water.
CH139367D 1927-10-25 1928-09-27 Process for the preparation of 4- (oxyethyl) -amino-1-oxybenzene-2-carboxylic acid. CH139367A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH132029T 1927-10-25
DE139367X 1927-11-12

Publications (1)

Publication Number Publication Date
CH139367A true CH139367A (en) 1930-04-15

Family

ID=25711736

Family Applications (1)

Application Number Title Priority Date Filing Date
CH139367D CH139367A (en) 1927-10-25 1928-09-27 Process for the preparation of 4- (oxyethyl) -amino-1-oxybenzene-2-carboxylic acid.

Country Status (1)

Country Link
CH (1) CH139367A (en)

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