DEP0026804DA - Process for the preparation of α-keto-O-oxycarboxylic acids. - Google Patents
Process for the preparation of α-keto-O-oxycarboxylic acids.Info
- Publication number
- DEP0026804DA DEP0026804DA DEP0026804DA DE P0026804D A DEP0026804D A DE P0026804DA DE P0026804D A DEP0026804D A DE P0026804DA
- Authority
- DE
- Germany
- Prior art keywords
- keto
- preparation
- oxycarboxylic acids
- rhein
- acids
- 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
- 239000002253 acid Substances 0.000 title claims description 5
- 150000007513 acids Chemical class 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 3
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 229930194542 Keto Natural products 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229930188620 butyrolactone Natural products 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000004715 keto acids Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000003901 oxalic acid esters Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- LZMSXDHGHZKXJD-VJANTYMQSA-N trypanothione disulfide Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@H]1CSSC[C@H](NC(=O)CC[C@H](N)C(O)=O)C(=O)NCC(=O)NCCCNCCCCNC(=O)CNC1=O LZMSXDHGHZKXJD-VJANTYMQSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Description
NOLL· A-M. NOLL AM.
CHEMISCHE FABRIKEN ■ (22b) LUDWIGSHAFEN AM RHEIN Rulnummcrn: Ze 301, 302 und 310 ■ Drahtanschrift: Knoll Ludwlgshalenrhein ■ Postscheckkonto: Ludwigshalen am Rhein Nr. 151 . Bankkonten in Ludwigshaien am Rhein: Giro· konto51/8i bei der Landeszentralbank. Rheinische Kreditbank, Bayerische Hypotheken, und Wechselbank · Bankkonto inMannheim: Allgemeine BankgesellsdiaU ■ PostschlieBiachCHEMISCHE FABRIKEN ■ (22b) LUDWIGSHAFEN AM RHEIN Rulnummcrn: Ze 301, 302 and 310 ■ Wire address: Knoll Ludwlgshalenrhein ■ Postal check account: Ludwigshalen am Rhein No. 151. Bank accounts in Ludwigshaien am Rhein: Giro account51 / 8i at the state central bank. Rheinische Kreditbank, Bayerische Hypotheken, and Wechselbank · Bank account in Mannheim: Allgemeine BankgesellsdiaU ■ PostschlieBiach
Patent -AbteilungPatent department
Verfahren zur Berstellang von ft—Keto—rt-oacyoarbonsauren»Process for the preparation of ft-keto-rt-oacyoarboxylic acids »
Es.wurde gefand.en@ dasa man oc-Eeto-d-oxy-fcarbon-It.was found.en @ dasa man oc-Eeto-d-oxy-fcarbon-
säareB bsw® deren ^-Laktone in hoher Ausbeute dadurch her~ stellen kann, dass man auf oc-CKeto^oarbalkoxyJ-y-laktone verdünnte Mineralsöuren einwirken lässt® Dabei spielt sich die folgende Reaktion ab:säareB bsw® produce their ^ -lactones in high yield as a result can put that on oc-CKeto ^ oarbalkoxyJ-y-lactones Allowing diluted mineral acids to take effect the following response:
I2C--CH - CO · COOl CH2 - GHg - GO - COOH *I 2 C - CH - CO COOL CH 2 - GHg - GO - COOH *
CO > HCO> H
Diese üiasetsuag ist insofern seüx überras oil end, als y-Lakto·» ae im Baffi"eii Medium pz^aktiscli aieiit in Form der freien γ-Oxy· säuren vorliegen komnem,® sondern nur in der laktonisierten' Fo rs®This is so far üiasetsuag seüx überras oil end, komnem exist as y-lacto · "ae in Baffi" eii medium pz ^ aktiscli aieiit in the free γ-oxy · acids, ® but only in the laktonisierten 'Fo RS®
Die o:-(Keto^öartealko3Ey)-y~la3£toae sind durch Eon» von y-Laktonen sit öxalsäareester leicht herstell»The o :-( Keto ^ öartealko3Ey) -y ~ la3 £ toae are easily produced by Eon » of y-lactones sit oxalic acid esters»
Die erfindangsgemäss herstellbaren cccarbonsäuren sind, wertvolle Zwischenprodukte feei der Synthe se von Aminosäuren® So lässt sich euB® oc-Keto-tZ säure durch Heduktionskondensation mit 'Ammoniak in. die cc—aminovaleriansäure überfuhren9 deren Hydrochloric! durch A spaltung τοη Chlorwasserstoff in d^l-PreliB übergeht«The erfindangsgemäss produced cccarbonsäuren are useful intermediates feei the Synthe se of Aminosäuren® So can euB® oc-keto acid by tZ Heduktionskondensation with 'ammonia in. The cc-aminovaleric acid ran down their 9 Hydrochloric! by cleavage τοη hydrogen chloride passes into d ^ l-PreliB "
M O Έα MjMO Έα Mj
CHEMISCHE FABRIKEN ■ (22b) LUDWIGSHAFEN AM RHEINCHEMICAL FACTORY ■ (22b) LUDWIGSHAFEN AM RHEIN
Rufnummern: Ze 301, 302 und 310 · Drahtanschrift: Knoll Ludwigshafenrhein · Postscheckkonto: Ludwigshafen am Rhein Nr. 151 · Bankkonten in Ludwigshaien am Rhein: Girokonto 51/81 bei der Landeszentralbank. Rheinische Kreditbank, Bayerische Hypotheken- und Wediselbank ■ Bankkonto in Mannheim: Allgemeine Bankgesellschaft · PostschließfachTelephone numbers: Ze 301, 302 and 310 · Wire address: Knoll Ludwigshafenrhein · Postal checking account: Ludwigshafen am Rhein No. 151 · Bank accounts in Ludwigshaien am Rhein: current account 51/81 at the state central bank. Rheinische Kreditbank, Bayerische Hypotheken- und Wediselbank ■ Bank account in Mannheim: Allgemeine Bankgesellschaft · Postfachfach
Patent-Abteilung ^, O mi ■ Patent Department ^, O mi ■
Beispiel ζ Example ζ
160 g &-(KetoearbäthQxy)-Y-butyralaktoxi9 hergestellt durch Kondensation von Butyrolakton mit Oxale.ster., werden mit 300 ecm 2£>n-Schwe£elsäure bis zum .Aufhören der Kohlensäureentwicklung «a-Sückfluss sum öieden erhitzt« wobei sicJri molare Mengen Kohlensäure abspalten* Zur Isolierung der Ketosäure als Ifoenyihydrazon vd.rd die scliwefelsaiare Lösung mit Matriömasetat abgestumpft und mit 108 g Ehenylhy* drazin versa tsst, worauf sich unter Erwänaung ein OeI atecliei« de*« Die Mischung wird noch-einige Seit auf dem. Wasserbaderwärmt^ darauf abkühlen lassen^, flae OeI abgetrennt and die wässrige Schicht aiisgeäthert® Pi? vereinigten Oelanteile werden nach ferdarapfong des Aethers mit 500 ecm 20^iger SaIesäare versetzt, wobei das OeI unter .Erwärmung in Lösung geht und alsbald das Pnenyliiydrazon des cu^Ket vom P,-178° atiskristallisierto Ausbeute:160 g of & - (KetoearbäthQxy) -Y-butyralaktoxi9 produced by the condensation of butyrolactone with Oxale.ster., Are heated with 300 ecm 2 £> n-sulfuric acid until the evolution of carbonic acid "a-reflux" is heated to boiling "whereby sicJri secede molar amounts of carbon dioxide * to isolate the keto acid as the Ifoenyihydrazon scliwefelsaiare solution Matriömasetat vd.rd jaded and g with 108 Ehenylhy * Drazin versa TSST, followed by a Erwänaung oil atecliei "de * is" the mixture still-some since on the . Warmed water bath ^ then let cool ^, the oil separated and the aqueous layer aiisgeäthert® Pi? combined oil components are mixed with 500 ecm of 20% SaIesäare after ferdarapfong the ether, whereby the oil goes into solution under heating and immediately the pnenylydrazone of the cu ^ ket from the P, -178 ° atiscrystallisierto yield:
Claims (1)
Family
ID=
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