DEC0000742MA - Process for the preparation of yγ- (1-oxynaphthyl- (4) - y γ-keto-butyric acid - Google Patents
Process for the preparation of yγ- (1-oxynaphthyl- (4) - y γ-keto-butyric acidInfo
- Publication number
- DEC0000742MA DEC0000742MA DEC0000742MA DE C0000742M A DEC0000742M A DE C0000742MA DE C0000742M A DEC0000742M A DE C0000742MA
- Authority
- DE
- Germany
- Prior art keywords
- butyric acid
- keto
- oxynaphthyl
- preparation
- aqueous
- 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
Links
- 238000000034 method Methods 0.000 title claims description 7
- UIUJIQZEACWQSV-UHFFFAOYSA-N succinic semialdehyde Chemical compound OC(=O)CCC=O UIUJIQZEACWQSV-UHFFFAOYSA-N 0.000 title 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 4
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- -1 methoxy - Chemical class 0.000 claims description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims 2
- 229930194542 Keto Natural products 0.000 claims 1
- 239000001582 butter acid Substances 0.000 claims 1
- 125000000468 ketone group Chemical group 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- TYEYBOSBBBHJIV-UHFFFAOYSA-N 2-oxobutanoic acid Chemical compound CCC(=O)C(O)=O TYEYBOSBBBHJIV-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
Description
pStJi44lAKTIENGESELLSCHAFT, BASEL (SCHWEIZ)pStJi44lA KTIENGESELLSCH AFT, BASEL (SWITZERLAND)
ΟΐρΙ.-lng. E. SpianemannΟΐρΙ.-lng. E. Spianemann
Hamburg 36 Neuer Wd110, 4. Stock Uu Hamburg 36 Neuer Wd110, 4th floor Uu
Anruf 347900 Kl ^^T] ^ 2 9.HUiZ 1950Call 347900 Kl ^^ T] ^ 2 9.HUiZ 1950
Neuer \/a,l lü, '!,',I, ^New \ / a, l lü, '!,', I, ^
Case 263Λ/Ε/Ζ
DeutschlandCase 263Λ / Ε / Ζ
Germany
/i^-y - /V- ^Ky^yMÄ^ Verfahren zur Herstellung / i ^ -y - / V- ^ Ky ^ yMÄ ^ Method of manufacture
Es wurde gefunden, dass ein wertvolles Zwischenprodukt hergestellt werden kann, wenn man eine Verbindung der FormelIt has been found that a valuable intermediate can be prepared using a compound of the formula
Θ-AlkylΘ-alkyl
COCO
1)1)
GEL·GEL·
CH2
GOOHCH 2
GOOH
in wässerigem.alkalihydrojcydhaltigeiK Medium auf eine Temperatur von mindestens 100° erhitztHeated in an aqueous medium containing alkali metal hydroxide to a temperature of at least 100 °
Die bei diesem Verfahren als Ausgangsstoffe dienendenThe starting materials used in this process
können nach der in dercan after in the
deutschen Patentschrift 576.635 angegebenen Methode^durch Konden·= sation von oc=Naphtholallcyläthern mit Bernsteinsäureanhydrid in Gegenwart von Aluniniumchlorid hergestellt werden, Anstelle des dort angegebenen Nitrobenzols kann vorteilhaft Tetrachloräthan als Lösungs- baizw. Verdünnungsmittel verwendet werden, ZweckmessigGerman patent 576,635 specified method ^ by condensation = sation of oc = Naphtholallcyläthern with succinic anhydride in In the presence of aluminum chloride, tetrachloroethane can advantageously be used instead of the nitrobenzene specified there as a solution baizw. Diluents are used, suitably
ι pe
werden solche Alkoxy naphthfe=3r£?jSketobutt er säur en vertirendet, welche in der Alkoxygruppe nur wenige C-Atome enthalten, wie z.B. die
l=Propyloxy- oder vorzugsweise die 1-Aethoxf- und die l=Methozf=ι pe
such alkoxy naphthous acids are used which contain only a few carbon atoms in the alkoxy group, such as, for example, the 1 = propyloxy or preferably the 1-ethoxy and the 1 = methoxy =
ketobutt ersäur e.ketobutic acid e.
Die Erhitzung dieser Alkoxy verbindungen in wässerigem alkalihydroxid dhaltigem Medium auf eine Temperatur von mindestens 100° kann in wässerigen, alkalihydroxydhaltigert Lösungen verschiedener Konzentrationen, E.B. in einer wässerigen, 50$igen Natriumhydroxydlösung vorgenommen werden. Vorzugsweise wird bei 130=l60o und unter Druck gearbeitet.The heating of these alkoxy compounds in an aqueous medium containing alkali hydroxide to a temperature of at least 100 ° can be carried out in aqueous, alkali hydroxide-containing solutions of various concentrations, EB in an aqueous, 50% sodium hydroxide solution. It is preferred to work at 130 = 160 o and under pressure.
Das neue Zwischenprodukt entspricht der FormelThe new intermediate corresponds to the formula
Diese/l~Oxynaphth££fcfeisil=i 3"=ketobuttersäure erweist sich als wertvoll für die Herstellung von Azofarbstoffen.This / l ~ oxynaphth ££ fcfeisil = i 3 "= ketobutyric acid proves to be valuable for the production of azo dyes.
258 Teile (l-MethoacynaphthhüeJtJ/'-ketobutterBäupe mit 650 Teilen einer wässerigen, 30$lgen Katriumhydrosfd= lösung in einem eisernen Rührautoklav während 5 Stunden auf l40=l45° erhitzt. Dann wird abgekühlt und mit Salzsäure angesäuerto Man erhält 230 Teile rohe [l=Osynaphth^±±sa=^/'-ketobuttersäure vom Schmelzpunkt 210°, die gewünschtenfalls durch Umkristallisieren aus Alkohol gereinigt werden kann.258 parts (l-MethoacynaphthhüeJtJ / '- ketobutterBäupe with 650 parts of an aqueous, 30 $ long potassium hydrosfd = solution heated to 140 = 145 ° in an iron stirred autoclave for 5 hours. It is then cooled and acidified with hydrochloric acid 230 parts of crude [l = Osynaphth ^ ± sa = ^ / '- ketobutyric acid with a melting point of 210 ° are obtained, which, if desired, are obtained Recrystallizing from alcohol can be purified.
Claims (4)
Family
ID=
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