CH205415A - Process for the preparation of 2- (4'-phenylphenoxy) -5-nitrobenzaldehyde. - Google Patents

Process for the preparation of 2- (4'-phenylphenoxy) -5-nitrobenzaldehyde.

Info

Publication number
CH205415A
CH205415A CH205415DA CH205415A CH 205415 A CH205415 A CH 205415A CH 205415D A CH205415D A CH 205415DA CH 205415 A CH205415 A CH 205415A
Authority
CH
Switzerland
Prior art keywords
nitrobenzaldehyde
preparation
oxydiphenyl
phenylphenoxy
water
Prior art date
Application number
Other languages
German (de)
Inventor
A-G J R Geigy
Original Assignee
Geigy Ag J R
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 Geigy Ag J R filed Critical Geigy Ag J R
Publication of CH205415A publication Critical patent/CH205415A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
    • C07C201/06—Preparation of nitro compounds
    • C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups

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

Description

  

  Verfahren zur Darstellung von     2-(4'-Phenylphenogy)-5-nitrobenzaldehyd.       Es     wurde        gefunden,    dass     durch    Umset  zung der     Alkalisalze    des     p-Oxydiphenyls     mit     2-Chlor-5-nitrobenzaldehyd    in sehr guter  Ausbeute     2-(4'-Phenyl-phenoxy)-5-nitrobenz-          aldehyd    entsteht.

   Die neue     Verbindung    wird  als feste, schwach bräunlich gefärbte, harz  artige Masse erhalten, die in Wasser unlös  lich     ist,    sehr schwer löslich ist in Benzin,  leicht löslich in Äther, Alkohol, Aceton, Ben  zol und mit konzentrierter Schwefelsäure eine  intensiv dunkelrote     Färbung    gibt. Sie soll als  Zwischenprodukt in der     Farbstoffindustrie     Verwendung finden.

      <I>Beispiel:</I>    51 kg     p-Oxydiphenyl    werden mit der zur  Salzbildung nötigen Menge Natronlauge  (1 Mal)     versetzt        bis    zur schwach     ätzalkaJi-          schen    Reaktion, dann mit weiteren 2 kg     p-          Oxydiphenyl,    56 kg     2-Chlor-5-nitrobenzalde-          hyd    und soviel Wasser, dass das Volumen  etwa 300 Liter beträgt.

       INTach    8- bis     10-          stündigem    Kochen und Rühren unter Rück  fluss ist die     lackmusalkalische    Reaktion ver  schwunden und die Umsetzung vollendet.    Überschüssiges p -     Oxydiphenyl    wird durch       Ausziehen    mit verdünntem Alkali, ein allfäl  liger Überschuss an Aldehyd durch     Wasser-          @dampf        entfernt.    Der     gwehmolzene        neue    Al  dehyd erstarrt in der     gälte    zu     einer    schwach  bräunlich gefärbten, harzartigen Masse.

   Er  ist unlöslich     in    Wasser, sehr schwer löslich  in     Benzin,    leicht löslich in Äther, Alkohol,  Aceton, Benzol,     intensiv    dunkelrot in konzen  trierter Schwefelsäure.



  Process for the preparation of 2- (4'-phenylphenogy) -5-nitrobenzaldehyde. It has been found that the reaction of the alkali metal salts of p-oxydiphenyl with 2-chloro-5-nitrobenzaldehyde results in very good yields of 2- (4'-phenyl-phenoxy) -5-nitrobenzaldehyde.

   The new compound is obtained as a solid, slightly brownish, resin-like mass that is insoluble in water, is very sparingly soluble in gasoline, is easily soluble in ether, alcohol, acetone, benzene and, with concentrated sulfuric acid, gives it an intense dark red color . It should be used as an intermediate in the dye industry.

      <I> Example: </I> 51 kg of p-oxydiphenyl are mixed with the amount of sodium hydroxide solution necessary for salt formation (once) until a weakly caustic reaction occurs, then with another 2 kg of p-oxydiphenyl, 56 kg of 2-chlorine 5-nitrobenzaldehyde and enough water that the volume is about 300 liters.

       INT After 8 to 10 hours of boiling and stirring under reflux, the litmus alkaline reaction has disappeared and the conversion is complete. Excess p-oxydiphenyl is removed by exhaustion with dilute alkali, and any excess of aldehyde is removed with steam. The gwolzene new aldehyde solidifies in the cold to a pale brownish colored, resinous mass.

   It is insoluble in water, very sparingly soluble in gasoline, easily soluble in ether, alcohol, acetone, benzene, intensely dark red in concentrated sulfuric acid.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung von 2 - (4' - Phenyl - phenoxy) - 5 - nitrobenzaldehyd, da durch gekennzeichnet, dass man ein Alkali salz des p-Oxydiphenyls mit 2-Chlor-5-nitro- benzaldehyd umsetzt. PATENT CLAIM: Process for the preparation of 2 - (4 '- phenyl - phenoxy) - 5 - nitrobenzaldehyde, characterized in that an alkali salt of p-oxydiphenyl is reacted with 2-chloro-5-nitrobenzaldehyde. Die neue Verbindung wird als feste, schwach bräunlich gefärbte, harzartige Masse erhalten, die in Wasser un löslich ist, sehr schwer löslich in Benzin, leicht löslich in Äther, Alkohol, Aceton, Ben zol ist und mit konzentrierter Schwefelsäure eine intensiv dunkelrote Färbung gibt. The new compound is obtained as a solid, slightly brownish colored, resin-like mass that is insoluble in water, very sparingly soluble in gasoline, easily soluble in ether, alcohol, acetone, benzene and gives an intense dark red color with concentrated sulfuric acid.
CH205415D 1936-02-29 1936-12-04 Process for the preparation of 2- (4'-phenylphenoxy) -5-nitrobenzaldehyde. CH205415A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE205415X 1936-02-29
CH193922T 1936-12-04

Publications (1)

Publication Number Publication Date
CH205415A true CH205415A (en) 1939-06-15

Family

ID=25722607

Family Applications (1)

Application Number Title Priority Date Filing Date
CH205415D CH205415A (en) 1936-02-29 1936-12-04 Process for the preparation of 2- (4'-phenylphenoxy) -5-nitrobenzaldehyde.

Country Status (1)

Country Link
CH (1) CH205415A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0052836A1 (en) * 1980-11-22 1982-06-02 Hoechst Aktiengesellschaft Phenoxybenzaldehydes and process for their preparation

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0052836A1 (en) * 1980-11-22 1982-06-02 Hoechst Aktiengesellschaft Phenoxybenzaldehydes and process for their preparation

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