DE72806C - Process for the preparation of carbonic acid esters of catechol and its monoalkyl ethers - Google Patents

Process for the preparation of carbonic acid esters of catechol and its monoalkyl ethers

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Publication number
DE72806C
DE72806C DENDAT72806D DE72806DA DE72806C DE 72806 C DE72806 C DE 72806C DE NDAT72806 D DENDAT72806 D DE NDAT72806D DE 72806D A DE72806D A DE 72806DA DE 72806 C DE72806 C DE 72806C
Authority
DE
Germany
Prior art keywords
ether
catechol
phenols
carbonic acid
carbonate
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 - Lifetime
Application number
DENDAT72806D
Other languages
German (de)
Original Assignee
Firma Dr. F. VON HEYDEN NACHFOLGER in Radebeul bei Dresden
Publication of DE72806C publication Critical patent/DE72806C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/96—Esters of carbonic or haloformic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C68/00—Preparation of esters of carbonic or haloformic acids
    • C07C68/02—Preparation of esters of carbonic or haloformic acids from phosgene or haloformates

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

Description

KAISERLICHESIMPERIAL

PATENTAMT.PATENT OFFICE.

In den Patenten Nr. 5812g, 60716 und 61848 wurde gezeigt, dafs man aus den in ätherischen Oelen vorkommenden Stoffen brauchbare Arzneistoffe erhält durch Ueberführung in die Carbonate.It was shown in Patents Nos. 5812g, 60716 and 61848 that one can obtain from the in essential oils occurring substances obtained usable medicinal substances by conversion into the carbonates.

In gleicher Weise wurde aus anderen, nicht in ätherischen Oelen vorkommenden Phenolen durch Ueberführung in die Carbonate Arzneistoffe gewonnen, welche vor den Ausgangsproducten, den freien Phenolen, dadurch ausgezeichnet sind, dafs sie neutral, indifferent gegen Schleimhäute und fast ungiftig sind und frei von Geschmack, Geruch, Aetzwirkung.In the same way, phenols not found in essential oils became phenols Drugs obtained by conversion into the carbonates, which precede the starting products, the free phenols, are distinguished by the fact that they are neutral, indifferent against mucous membranes and are almost non-toxic and free from taste, odor and caustic effects.

Diese neuen Arzneistoffe zeichnen sich von denen der obigen Patente durch andere neue physiologische Wirkungen aus.These new drugs are distinguished from those of the above patents by other new ones physiological effects.

Folgende Phenole dienten als Rohstoffe:The following phenols were used as raw materials:

Brenzcatechin , Brenzcatechinmono - äthyl-, -propyl-, -isopropyl-, -butyl-, -isobutyl- oder -amyläther oder Homobrenzcatechinmethyläther (hergestellt aus o-Amido-p-kresolmethyläther durch Ersatz der Amidogruppe durch Hydroxyl).Pyrocatechol, pyrocatechol mono-ethyl-, -propyl-, -isopropyl-, -butyl-, -isobutyl- or -amyl ether or homocatechol methyl ether (made from o-amido-p-cresol methyl ether by replacing the amido group with hydroxyl).

Die Ueberführung dieser Phenole in die Carbonate erfolgt nach bekannten, z. B. in den oben genannten Patenten genau beschriebenen Verfahren, also durch Einwirkung von Phosgen auf die Phenole oder deren Salze nach den Gleichungen:The conversion of these phenols into the carbonates takes place according to known methods, e.g. Tie The above-mentioned patents precisely describe the process, i.e. by the action of phosgene on the phenols or their salts according to the equations:

2 C6 H&0 H+ 'C O Cl2 2 C 6 H & 0 H + 'CO Cl 2

= CO (O C6 HJ2 + 2 H Cl, = CO (O C 6 HJ 2 + 2 H Cl,

2C6H5ONa+ CO Cl2 = C O (O C6 H5J2 + 2 Na Cl. 2C 6 H 5 ONa + CO Cl 2 = CO (O C 6 H 5 Y 2 + 2 Na Cl.

Z. B. ι Mol. Brenzcatechin wird mit 1 Mol. Phosgen eventuell bei Gegenwart eines als Lösungsmittel dienenden indifferenten Stoffes, wie Benzol, im Druckgefäfs auf 130 bis 1800C. erhitzt. Aus dem Reactionsproduct wird das Benzol mit Wasserdampf abdestillirt. Das zurückbleibende rohe Brenzcatechincarbonat wird aus Alkohol umkrystallisirt und in farblosen Krystallen vom Schmelzpunkt 1200C. erhalten.For example, 1 mole of pyrocatechol is heated to 130 to 180 ° C. in a pressure vessel with 1 mole of phosgene, possibly in the presence of an inert substance, such as benzene, serving as a solvent. The benzene is distilled off from the reaction product with steam. The residual crude pyrocatechol carbonate is recrystallized from alcohol and obtain 120 0 C. colorless crystals of melting point.

Statt die Reaction, wie beschrieben, in einer Phase verlaufen zu lassen, kann man die durch die Gleichungen:Instead of letting the reaction run in one phase, as described, one can go through it the equations:

C1-H5OH+ CO Cl2 C 1 -H 5 OH + CO Cl 2

= C6H5OCOCl + HCl, = C 6 H 5 OCOCl + HCl,

C9H5O CO Cl +C6H5 OHC 9 H 5 O CO Cl + C 6 H 5 OH

= (C6H5OJ2CO + H Cl = (C 6 H 5 OJ 2 CO + H Cl

gekennzeichneten Phasen auch getrennt ausführen, also erst das Phenoxycarbonylchlorid darstellen und dieses dann mit einem zweiten Molecül Phenol oder Phenolsalz reagiren lassen.also carry out the marked phases separately, i.e. first the phenoxycarbonyl chloride and then react with a second molecule of phenol or phenol salt permit.

Für die meisten Fälle ist es bequemer, die bei der Reaction entstehende Salzsäure zu binden, indem man das Phosgen mit Phenolsalzen reagiren läfst.In most cases it is more convenient to add the hydrochloric acid produced in the reaction bind by allowing the phosgene to react with phenol salts.

Z. B. Eine Lösung von Brenzcatechinmonoäthyläther in der äquivalenten Menge Natronlauge wird mit Phosgen bis zur neutralen Reaction gesättigt. Der hierbei sich ausscheidende kohlensaure Brenzcatechinmonoäthyläther wird durch Umkrystallisiren aus Alkohol gereinigtE.g. a solution of catechol monoethyl ether in the equivalent amount of sodium hydroxide solution is saturated with phosgene until the reaction is neutral. The here eliminated Carbonic catechol monoethyl ether is purified from alcohol by recrystallization

Claims (1)

und bildet farblose
punkt 8i° C.and forms colorless
point 8i ° C. Krystalle vom Scbmelz-Es wurden auf
bonate hergestellt:Crystals from the melt-it opened
bonate produced: diese Weise folgende Carthis way following car i. CO (O C6 H4O C2 HJ2 kohlensaurer Brenzcatechinmonoä'thyläther Schmp.i. CO (O C 6 H 4 OC 2 HJ 2 carbonate pyrocatechol monoethyl ether mp. ( ( 66th 4 2 5^ CO(O C6H4O C3 H1J2 CO(O C6H4O C3H7J2 CO(O C6H4OC4HJ, CO(OC6H4OC4H[X CO(OC6H4OC5HnJ2 4 2 5 ^ CO (OC 6 H 4 OC 3 H 1 J 2 CO (OC 6 H 4 OC 3 H 7 J 2 CO (OC 6 H 4 OC 4 HJ, CO (OC 6 H 4 OC 4 H [X CO (OC 6 H 4 OC 5 H n J 2 0(0 ( propyläther
isopropylätherpropyl ether
isopropyl ether butyläther butyl ether isobutyläther .
amyläther isobutyl ether.
amyl ether Ca C a kohlensaures Brenzcatechincarbonate catechol CHCH 8. C0\ CK 8. C0 \ C K H3OH 3 O OCHOCH kohlensaurer Homobrenzcatechinmonomethyläthercarbonate homocatechol monomethyl ether 60 °60 ° 49° 48°49 ° 48 ° 5'° 60 °5 '° 60 ° 120°120 ° 1351 135 1 Diese Stoffe sind bisher noch nicht dargestellt gewesen, bis auf das kohlensaure Brenzcatechin, welches früher auf andere umständlichere und theuerere Weise erhalten wurde.These substances have not yet been shown, with the exception of the carbonic catechol, which was previously obtained in other more cumbersome and expensive ways. Die obigen Stoffe sind farblos, unlöslich in Wasser, löslich in Alkohol und Aether und zeichnen sich vor den freien Phenolen durch ihre neutrale Reaction, ihr indifferentes Verhalten gegen die Haut, durch das Fehlen von ätzenden Eigenschaften, von Geruch und Geschmack aus. Sie sind deshalb und wegen ihrer geringen Giftigkeit sehr brauchbare Arzneistoffe, welche im thierischen Organismus in Kohlensäure und die verschiedenen Phenole zerlegt werden, denen meist specifische Wirkungen entsprechen.The above substances are colorless, insoluble in water, soluble in alcohol and ether and stand out from the free phenols by their neutral reaction, their indifferent behavior against the skin, due to the lack of caustic properties, smell and taste the end. Because of this, and because of their low toxicity, they are very useful medicinal substances which are found in the animal organism are broken down into carbonic acid and the various phenols, most of which have specific effects correspond. Dieselbe Zerlegung erfolgt beim Behandeln mit Natronlauge.The same decomposition takes place when treating with caustic soda. Pa τ en τ-Anspruch:Pa τ en τ claim: Verfahren zur Darstellung von Kohlensäureestern des Brenzcatechins, Homobrenzcatechins oder ihrer Monoalkyläther, darin bestehend, dafs man die letzteren Phenole als solche oder in Form ihrer Salze mit Phosgen behandelt.Process for the preparation of carbonic acid esters of catechol, homocatechol or their monoalkyl ethers, consisting in using the latter phenols as such or treated with phosgene in the form of their salts.
DENDAT72806D Process for the preparation of carbonic acid esters of catechol and its monoalkyl ethers Expired - Lifetime DE72806C (en)

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DE72806C true DE72806C (en)

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Family Applications (1)

Application Number Title Priority Date Filing Date
DENDAT72806D Expired - Lifetime DE72806C (en) Process for the preparation of carbonic acid esters of catechol and its monoalkyl ethers

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DE (1) DE72806C (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007144169A2 (en) * 2006-06-16 2007-12-21 Schwarz Pharma Ag Entacapone-derivatives

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007144169A2 (en) * 2006-06-16 2007-12-21 Schwarz Pharma Ag Entacapone-derivatives
WO2007144169A3 (en) * 2006-06-16 2008-05-22 Sanol Arznei Schwarz Gmbh Entacapone-derivatives

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