CH205419A - Process for the preparation of 4- (4'-methylphenoxy) -5-nitrobenzaldehyde. - Google Patents

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

Info

Publication number
CH205419A
CH205419A CH205419DA CH205419A CH 205419 A CH205419 A CH 205419A CH 205419D A CH205419D A CH 205419DA CH 205419 A CH205419 A CH 205419A
Authority
CH
Switzerland
Prior art keywords
nitrobenzaldehyde
methylphenoxy
preparation
water
gasoline
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 CH205419A publication Critical patent/CH205419A/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     4-(4'-Nethylphenogy)-ö-nitrobenzaldehyd.       Es wurde gefunden, dass durch Umsetzung  von     Alkali-p-kresolat    mit     4-Chlor-5-nitrobenz-          aldehyd    in sehr guter Ausbeute     4-(4'-Methyl-          phenoxy)-5-nitrobenzaldehydentsteht.    Die neue  Verbindung kristallisiert in feinen, fast farb  losen Nadeln vom Schmelzpunkt 112 . Sie  ist unlöslich in Wasser, sehr schwer löslich  in Benzin, leicht löslich in Äther, Alkohol,  Aceton, Benzol und gibt mit konzentrierter  Schwefelsäure eine intensiv     gelbolive    Fär  bung. Sie soll als Zwischenprodukt in der       Farbstoffindustrie    Verwendung finden.

    



  <I>Beispiel:</I>  32,4 kg     p-Kresol    werden mit der zur       Phenolatbildung    nötigen Menge Natronlauge  versetzt bis zur schwach     ätzalkalischen    Re  aktion, dann mit weiteren 2 kg     p-gresol,     56 kg     4-Chlor-5-nitrobenzaldehyd    und soviel  Wasser, dass das Volumen etwa 300 Liter     be-          trägt.        Nach     Kochen und Rüh  ren unter     Rückfluss    ist die     lackmusalkalische     Reaktion verschwunden und die Umsetzung  vollendet.

   Überschüssiges     p-Kresol    wird durch         Wasserdampfdestillation    entfernt, ebenso ein  allfälliger Überschuss der Aldehyds. Der ge  schmolzene neue Aldehyd erstarrt in der gälte  zu einer schwach gelblich gefärbten, kristal  linischen     Masse.    Er kristallisiert in feinen  Nadeln vom     Smp.    1120 und ist unlöslich in  Wasser, sehr schwer löslich in Benzin, leicht  löslich in Äther, Alkohol, Aceton, Benzol,  intensiv     gelbolive    in konzentrierter Schwefel  säure.



  Process for the preparation of 4- (4'-Nethylphenogy) -ö-nitrobenzaldehyde. It has been found that the reaction of alkali metal p-cresolate with 4-chloro-5-nitrobenzaldehyde gives 4- (4'-methylphenoxy) -5-nitrobenzaldehyde in very good yield. The new compound crystallizes in fine, almost colorless needles with a melting point of 112. It is insoluble in water, very sparingly soluble in gasoline, easily soluble in ether, alcohol, acetone, benzene and gives an intense yellow olive color with concentrated sulfuric acid. It should be used as an intermediate in the dye industry.

    



  <I> Example: </I> 32.4 kg of p-cresol are mixed with the amount of sodium hydroxide solution necessary for phenolate formation until the reaction is weakly alkaline, then with another 2 kg of p-gresol, 56 kg of 4-chloro-5-nitrobenzaldehyde and enough water that the volume is around 300 liters. After boiling and stirring under reflux, the litmus alkaline reaction has disappeared and the conversion is complete.

   Excess p-cresol is removed by steam distillation, as is any excess of the aldehyde. The molten new aldehyde solidifies in the cold to a pale yellowish colored, crystalline mass. It crystallizes in fine needles with a melting point of 1120 and is insoluble in water, very sparingly soluble in gasoline, easily soluble in ether, alcohol, acetone, benzene, intense yellow olive in concentrated sulfuric acid.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung von 4-(4'-Me- thylphenoxy)-5-nitrobenzaldehyd, dadurch ge kennzeichnet, dass man Alkali-p-kresolat mit 4-Chlor-5-nitrobenzaldehyd umsetzt. Die neue Verbindung kristallisiert in feinen, fast far blosen Nadeln vom Schmelzpunkt 1120. Sie ist unlöslich in Wasser, sehr schwer löslich in Benzin, leicht löslich in Äther, Alkohol, Aceton, Benzol und gibt mit konzentrierter Schwefelsäure eineintensivgelbolive Färbung. PATENT CLAIM: Process for the preparation of 4- (4'-methylphenoxy) -5-nitrobenzaldehyde, characterized in that alkali metal p-cresolate is reacted with 4-chloro-5-nitrobenzaldehyde. The new compound crystallizes in fine, almost colorless needles with a melting point of 1120. It is insoluble in water, very sparingly soluble in gasoline, easily soluble in ether, alcohol, acetone, benzene and gives an intense yellow olive color with concentrated sulfuric acid.
CH205419D 1936-02-29 1936-12-04 Process for the preparation of 4- (4'-methylphenoxy) -5-nitrobenzaldehyde. CH205419A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE205419X 1936-02-29
CH193922T 1936-12-04

Publications (1)

Publication Number Publication Date
CH205419A true CH205419A (en) 1939-06-15

Family

ID=25722611

Family Applications (1)

Application Number Title Priority Date Filing Date
CH205419D CH205419A (en) 1936-02-29 1936-12-04 Process for the preparation of 4- (4'-methylphenoxy) -5-nitrobenzaldehyde.

Country Status (1)

Country Link
CH (1) CH205419A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2906779A (en) * 1957-03-19 1959-09-29 Michel Raymond Preparation of 3-nitro-4 (4'-methoxyphenoxy)-benzaldehyde

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2906779A (en) * 1957-03-19 1959-09-29 Michel Raymond Preparation of 3-nitro-4 (4'-methoxyphenoxy)-benzaldehyde

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