DE361043C - Process for the preparation of aldehydes of the anthraquinone series - Google Patents

Process for the preparation of aldehydes of the anthraquinone series

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Publication number
DE361043C
DE361043C DEF47500D DEF0047500D DE361043C DE 361043 C DE361043 C DE 361043C DE F47500 D DEF47500 D DE F47500D DE F0047500 D DEF0047500 D DE F0047500D DE 361043 C DE361043 C DE 361043C
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DE
Germany
Prior art keywords
aldehydes
preparation
parts
anthraquinone series
acetic acid
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
DEF47500D
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German (de)
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.)
Hoechst AG
Original Assignee
Hoechst AG
Publication date
Priority to DEF47500D priority Critical patent/DE361043C/en
Application granted granted Critical
Publication of DE361043C publication Critical patent/DE361043C/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C50/00—Quinones
    • C07C50/38—Quinones containing —CHO or non—quinoid keto groups

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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 Aldehyden der Anthrachinonreihe. Durch die Patentschrift i7-t984 ist es bekannt, daß die u, - Dihalogenderivate des ß-:@Iethylanthrachinöns durch Erhitzen mit konzentrierter Sch@@vofelsäure, mit oder ohne Zusatz von Borsäure, in ßi-Ant:hracliinonalde:hyde übergeführt werden.Process for the preparation of aldehydes of the anthraquinone series. By the patent i7-t984 it is known that the u, - dihalogen derivatives of ß -: @ ethylanthraquinones by heating with concentrated sch @@ vofelic acid, with or without the addition of boric acid, be transferred into ßi-Ant: hracliinonalde: hyde.

Es .,#vurcle nun .gefunden, daß w - Dihalogen--P,=methyia,ntrlirachinon und dessen Substitutionsprod.ukte sehr leicht durch Erhitzen in Eisessig bei Gegenwart gewisser Metallsalze zu den entsprechenden Anthrachinonaldehyden verseift werden. Als besonders wirksam erwiesen sich z. B. Eisenrlilori.d, Chlorzink und Ouecksilberacetat.It., # Vurcle now. Found that w - dihalogen - P, = methyia, ntrlirachinon and its substitution products very easily by heating in glacial acetic acid in the presence certain metal salts to be saponified to the corresponding anthraquinone hydrides. To be particularly effective z. B. Eisenrlilori.d, zinc chloride and mercury acetate.

Beispiele. i. io Teile u,-Dibrom-ß methyl:anthracliinon, aus Toltiol umkristallisiert, :werden mit 3o Teilen Eisessig und i Teil wasserfreiem Risenchlorid 2 Stunden lang am Rückflußkühler erhitzt. Unter Entwicklung von Bromwasserstoff tritt Lösung ein. Das mit Wasser gefällte Produkt wird abfiltriert und gewaschen und dann mit verdünnter Natriumbisulfitlösung ausgekocht, wobei es nahezu vollständig in Lösung geht. Aus dem Filtrat fällt i\Zineralsäure in der Wärme reinen ß-Anthrachinonaldehyd mit 93 bis 9.4 Prozent :der theoretisch möglichen Ausbeute.Examples. i. io parts u, -dibromo-ß methyl: anthracliinon, from Toltiol recrystallized: are with 3o parts of glacial acetic acid and 1 part of anhydrous ferric chloride Heated under the reflux condenser for 2 hours. With evolution of hydrogen bromide solution occurs. The product precipitated with water is filtered off and washed and then boiled up with dilute sodium bisulfite solution, it being almost completely goes into solution. In the warmth, pure ß-anthraquinone aldehyde falls from the filtrate with 93 to 9.4 percent: the theoretically possible yield.

2. Wird in obigem Beispiel das Eisenchlorid durch 2 Teile Chlorzinkersetzt, so ist zur völligen Verseifung der Dibromv erbindung eine etwas längere Zeit notwendig. Das Ergebnis ist im übrigen das gleiche. 3. i9 Teile w4Dibrom-ß-lmethylantdhraahinon «-erden mit einer Lösung von i i Teilen Quecksilberoxyd i.n 5o Teilen Eisessig allmählich erwärmt, bis unter Aufkochen völlige Lösung, eintritt. Das mit Wasser gefällte Produkt wird filtriert, gewaschen und kurze Zeit mit roher Salzsäure aufgekocht. Die weitere Aufarbeitung erfolgt nach Beispiel r. Die Ausbeute an reinem ßJAld.ehyd beträgt 96 Prozent der Theorie.2. If, in the above example, the ferric chloride is replaced by 2 parts of zinc chloride, thus a somewhat longer time is necessary for the complete saponification of the dibromine compound. The result is otherwise the same. 3. 19 parts of w4-dibromo-β-1-methylantdhraahinone Earth gradually with a solution of i i parts of mercury oxide in 50 parts of glacial acetic acid heated until complete solution occurs with boiling. The product precipitated with water is filtered, washed and briefly boiled with crude hydrochloric acid. The other Work-up is carried out according to example r. The yield of pure β-aldehyde is 96 percent of theory.

.. io Teile rohes u,-Dibrom-2-methyl-3-chlonantbrachinon (vgl. - Ber. @d. Deutschen Chemischen Gesellschaft, Band 47, S. 558 u. 559) werden mit 8o Teilen Eisessig und 2 Teilen wasserfreiem Eisenchlorid so lange zum Sieden erhitzt, bis die :bald einsetzende Halogenwasserstoffentwicklung beendet ist. Das .Reaktionsprodukt wird mach Beispiel i auf 3-Chloranthraehinon-2-alclehyd weiterverarbeitet... io parts of crude u, -dibromo-2-methyl-3-chlonantbrachinon (cf. - Ber. @d. German Chemical Society, Volume 47, pp. 558 and 559) are made up of 80 parts Glacial acetic acid and 2 parts of anhydrous ferric chloride heated to the boil until the: soon onset of hydrogen halide evolution has ended. The. Reaction product is processed according to example i on 3-chloranthraehinone-2-alclehyd.

5. In gleicher Weise entsteht aus rohem u, - Dichlor-2-methyl-i-chlorantbrachinon (erhalten nach der Patentschrift 252578, Beispiel 2) .beim Erhitzen in Eisessig mit Eisenchlorid der i-Chloranthrachinon-2-aldehy cl (vgl. Patentschrift 174984, Beispiel 2).5. In the same way, crude u, - dichloro-2-methyl-i-chlorantbrachinone is formed (obtained according to patent specification 252578, example 2) when heated in glacial acetic acid with iron chloride of i-chloroanthraquinone-2-aldehyde cl (see patent specification 174984, Example 2).

Claims (1)

P ATRNT-ANSPRUcH: Verfahren zur Darstellung von Aldehyden der Anthrachinonreihe, dadurch gekennzeichnet, daß man co - Dihalogen-P)-lnethylanthrachinon öder dessen Derivate mit Eisessig, in Gegenwart von Metallsalizen, bei erhöhter Temperatur behandelt. Von dent Patentsucher ist als der Erfinder angegeben worden: P ATRNT CLAIM: Process for the preparation of aldehydes of the anthraquinone series, characterized in that co - dihalo-P) methylanthraquinone or its derivatives are treated with glacial acetic acid in the presence of metal salts at elevated temperature. The patent searcher has indicated as the inventor:
DEF47500D Process for the preparation of aldehydes of the anthraquinone series Expired DE361043C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEF47500D DE361043C (en) Process for the preparation of aldehydes of the anthraquinone series

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF47500D DE361043C (en) Process for the preparation of aldehydes of the anthraquinone series

Publications (1)

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DE361043C true DE361043C (en) 1922-10-09

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1153009B (en) * 1960-02-17 1963-08-22 Gen Aniline & Film Corp Process for the production of benzaldehydes

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1153009B (en) * 1960-02-17 1963-08-22 Gen Aniline & Film Corp Process for the production of benzaldehydes

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