DE423035C - Process for the preparation of 2-acetoxy-4-methoxybenzene-1-carboxylic acid - Google Patents

Process for the preparation of 2-acetoxy-4-methoxybenzene-1-carboxylic acid

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Publication number
DE423035C
DE423035C DEF55868D DEF0055868D DE423035C DE 423035 C DE423035 C DE 423035C DE F55868 D DEF55868 D DE F55868D DE F0055868 D DEF0055868 D DE F0055868D DE 423035 C DE423035 C DE 423035C
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DE
Germany
Prior art keywords
carboxylic acid
methoxybenzene
acetoxy
preparation
weight
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
Application number
DEF55868D
Other languages
German (de)
Inventor
Dr Fritz Schoenhoefer
Dr Werner Schulemann
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer AG
Original Assignee
Farbenfabriken Vorm Friedr Bayer and Co
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 Farbenfabriken Vorm Friedr Bayer and Co filed Critical Farbenfabriken Vorm Friedr Bayer and Co
Priority to DEF55868D priority Critical patent/DE423035C/en
Application granted granted Critical
Publication of DE423035C publication Critical patent/DE423035C/en
Expired 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
    • C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
    • C07C69/84—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring
    • C07C69/86—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring with esterified hydroxyl groups

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

Description

Verfahren zur Darstellung der 2-Acetoxy-4-mothoxybenzol-i-carbonsäure. In der Literatur sind Verbindungen vorn Schmelzpunkt i4o0 und 145 bis 147' (vgl. Ber.24 118911, S.2852, journ. of the chem. SOc- 107, S. 494) als :2-Acetoxy-4-methoxybenzol-i-carbonsäure beschrieben.Process for the preparation of 2-acetoxy-4-mothoxybenzene-i-carboxylic acid. In the literature, compounds with a melting point of 140 and 145 to 147 '(cf. Ber. 24 118911, p. 2852, journ. Of the chem. SOc-107, p. 494) are listed as: 2-acetoxy-4-methoxybenzene-i -carboxylic acid described.

Diese Verbindungen zeigen nach Versuchen cler Erfinder ein ungleichmäßiges Verhalten bei der physiologischen Erprobung und sind nach chemischen Feststellungen wechselnde Gemische aus der weiter unten zu beschreibenden, bisher unbekannten wahren Acetylverbindung und mehreren anderen therapeutisch minderwertigen Körpern, vor allem der Methoxysalicylomethoxysalicylsäure vom Schmelzpunkt 16o0.According to the inventors' experiments, these compounds show an uneven pattern Conduct during physiological testing and are based on chemical findings changing mixtures of the previously unknown true to be described below Acetyl compound and several other therapeutically inferior bodies especially methoxysalicylomethoxysalicylic acid with a melting point of 16o0.

Es wurde nun gefunden, daß die bisher noch unbekannte - ?,-Acetoxy-4-methoxybenzol-i-carbonsäure vom Schmelzpunkt iig bis 121' in reiner Form und von gleichmäßiger physiologischer Wirkung durch schonende Acetylierung der zugrunde liegenden 4-Methoxv-2-oxybenzol-i-carbonsäure erhalten werden kann, wenn man z. B. dafür Sorge trägt, daß die Reaktion unter Vermeidung stärkerer Wärmetönung vor sich geht.It has now been found that the hitherto unknown - ?, - Acetoxy-4-methoxybenzene-i-carboxylic acid from melting point iig to 121 'in pure form and of uniform physiological action through gentle acetylation of the underlying 4-methoxy-2-oxybenzene -i-carboxylic acid can be obtained if one z. B. ensures that the reaction takes place while avoiding stronger exothermicity.

Die so erhaltene neue Verbindung zeigt bei besserer Verträglichkeit eine stärkere temperaturherabsetzende und schmerzvermindernde Wirkung als die Acetylsalicylsäure, selbst wenn sie in kleineren Dosen als diese genommen wird. Beispiel i.The new compound thus obtained shows better compatibility a stronger temperature-reducing and pain-relieving effect than acetylsalicylic acid, even if taken in doses smaller than this. Example i.

168 Gewichtsteile 4-Methoxy-2-oxybenzoli-carbonsäure werden in 3oo Gewichtsteilen trockenem Äther gelöst und mit 115 Gewichtsteilen Essigsäureanhydrid etwa i bis il/" Tage am Rückflußkühler gekocht. Nach dem Verdampfen des Äthers erhält man ein rasch zu einem Kristallkuchen erstarrendes öl. Durch Umkristallisieren aus verdünntem Alkohol entstehen Nädelchen vom Schmelzpunkt iig bis 121'.168 parts by weight of 4-methoxy-2-oxybenzenecarboxylic acid are dissolved in 300 parts by weight of dry ether and refluxed with 115 parts by weight of acetic anhydride for about one to one-half days. After evaporation of the ether, an oil that rapidly solidifies to a crystal cake is obtained Recrystallization from dilute alcohol results in needles with a melting point of iig to 121 '.

Beispiel 2-.Example 2-.

168 Gewichtsteile 4-Methoxy-:2-oxybenzoli-carbonsäure werden in 6oo Gewichtsteilen Benzol angeschlämmt und zwei Tage mit 115 Gewichtsteilen Essigsäureanhydrid bei 3o bis 4o' gerührt. Es kristallisiert die im Beispiel i erhaltene Acetylverbindung aus, die aus Benzol umkristallisiert ebenfalls bei iig bis 121' schmilzt.168 parts by weight of 4-methoxy-: 2-oxybenzenecarboxylic acid are in 600 Parts by weight of benzene slurried and two days with 115 parts by weight of acetic anhydride stirred at 3o to 4o '. The acetyl compound obtained in Example i crystallizes out which, when recrystallized from benzene, also melts at iig to 121 '.

Beispiel 3. Example 3.

5o Gewichtsteile :2-OxY-4-methoxybenzoli-carbonsäure werden unter Kühlung in 2oo Gewichtsteilen.Pyridin gelöst. In diese Lösung läßt man unter starkem Rühren und Kühlen mit Kältemischung langsam die berechnete Menge Acetylchlorid zufließen. Nach il/, Tagen Stehen der Lösung bei Zimmertemperatur wird in eisgekühlte verdünnte Schwefelsäure gegossen, wo ' b - ei. ein weißer Niederschlag entsteht, der abgenutscht und wiederholt mit Wasser ausgewaschen wird. Nach dem Trocknen im Vakuum wird aus Benzol umkristallisiert.50 parts by weight: 2-OxY-4-methoxybenzenecarboxylic acid are dissolved in 2oo parts by weight of pyridine with cooling. The calculated amount of acetyl chloride is slowly poured into this solution with vigorous stirring and cooling with a cold mixture. After standing for one and a half days at room temperature, it is poured into ice-cold dilute sulfuric acid, where 'b - ei. a white precipitate is formed, which is filtered off with suction and washed out repeatedly with water. After drying in vacuo, it is recrystallized from benzene.

Claims (1)

PATENT-ANSPRUCII-Verfahren zur Darstellung der :2-Acet-OxY - 4 - methoxybenzol - i - carbonsäure, dadurch gekennzeichnet, daß man 4-Methoxy-:2-oxybenzol- i -carbonsäure einer schonenden Acetylierung unterwirft.PATENT-ANSPRUCII process for the preparation of: 2-Acet-OxY - 4 - methoxybenzene - i - carboxylic acid, characterized in that 4-methoxy-: 2-oxybenzene-i-carboxylic acid is subjected to a gentle acetylation.
DEF55868D 1924-04-05 1924-04-05 Process for the preparation of 2-acetoxy-4-methoxybenzene-1-carboxylic acid Expired DE423035C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEF55868D DE423035C (en) 1924-04-05 1924-04-05 Process for the preparation of 2-acetoxy-4-methoxybenzene-1-carboxylic acid

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF55868D DE423035C (en) 1924-04-05 1924-04-05 Process for the preparation of 2-acetoxy-4-methoxybenzene-1-carboxylic acid

Publications (1)

Publication Number Publication Date
DE423035C true DE423035C (en) 1925-12-18

Family

ID=7107808

Family Applications (1)

Application Number Title Priority Date Filing Date
DEF55868D Expired DE423035C (en) 1924-04-05 1924-04-05 Process for the preparation of 2-acetoxy-4-methoxybenzene-1-carboxylic acid

Country Status (1)

Country Link
DE (1) DE423035C (en)

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