DE423037C - Process for the preparation of dialkyl ethers of hydroquinone with a basic alkyl radical - Google Patents

Process for the preparation of dialkyl ethers of hydroquinone with a basic alkyl radical

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Publication number
DE423037C
DE423037C DEF55139D DEF0055139D DE423037C DE 423037 C DE423037 C DE 423037C DE F55139 D DEF55139 D DE F55139D DE F0055139 D DEF0055139 D DE F0055139D DE 423037 C DE423037 C DE 423037C
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DE
Germany
Prior art keywords
hydroquinone
preparation
alkyl radical
dialkyl ethers
basic
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
DEF55139D
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German (de)
Inventor
Dr Hans Hahl
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
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Filing date
Publication date
Application filed by Farbenfabriken Vorm Friedr Bayer and Co filed Critical Farbenfabriken Vorm Friedr Bayer and Co
Priority to DEF55139D priority Critical patent/DE423037C/en
Application granted granted Critical
Publication of DE423037C publication Critical patent/DE423037C/en
Expired legal-status Critical Current

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Description

Verfahren zur Darstellung von Dialkyläthern des Hydrochinons mit einem basischen Alkylrest. Es wurde gefunden, daß gesättigte Monoalkyläther des Hydrochinons mit einem basischen Oxalkylrest in der zweiten Phenolhydroxylgruppe ausgesprochene physiologische Eigenschaften zeigen. Die neuen Verbindungen haben sich als besonders wirksam erwiesen bei gewissen Erkrankungen des Herzens. Sie wirken blutdruckherabsetzend, verlangsamen den Puls und -übertreffen in dieser Hinsicht die analogen oder m-substituierten Verbindungen. Man kann sie in glatter Reaktion mit vorzüglicher Ausbeute in der Weise darstellen, daß man auf die gesättigten llonoalkyläther des Hy drochinons basische Alkylhalogenide, oder umgekehrt auf die 1lonoalkylaminoalkyläther dieses Phenols Alkylhalogenide, zweckmäßig bei Gegenwart alkalisch wirkender Mittel, einwirken läßt.Process for the preparation of dialkyl ethers of hydroquinone with a basic alkyl radical. It has been found that saturated monoalkyl ethers of hydroquinone pronounced with a basic oxalkyl radical in the second phenolic hydroxyl group show physiological properties. The new connections have proven to be special proven effective in certain diseases of the heart. They have a blood pressure lowering effect, slow down the pulse and outperform the analog or m-substituted in this regard Links. You can get them in smooth reaction with excellent yield in the Way to represent that one drochinons on the saturated Ilonoalkyläther des Hy basic alkyl halides, or vice versa to the 1lonoalkylaminoalkyl ethers this Phenol alkyl halides, expediently in the presence of alkaline agents, act leaves.

Beispiel i 3,7 Gewichtsteile Natrium werden in 5o Gewichtsteilen Alkohol aufgelöst und mit 2o Gewichtsteilen Hy drochinonmonomethyläther und 25' Gewichtsteilen Diäthylaminochloräthanol versetzt. Die Reaktion beginnt schon bei Zimmertemperatur und wird durch Erwärmen vervollständigt. Dann wird in Wasser gegossen, das sich abscheidende 01 abgehoben, getrocknet und destilliert. Unter i5mmDruck geht der Diäth_vlaminolithylhydrochinonmonomethyläther als farblose Flüssigkeit über, die mit Säuren nach den üblichen Methoden erhältliche gut kristallisierende Salze bildet. Das salzsaure Salz z. B. kristallisiert aus Essigester in farblosen Nadeln, die bei 121 bis I22° schmelzen. Beispiel e: ioo Gewichtsteile Hydrochinonmonodiäthvlaminoäthvläther werden mit 67 Gewichtsteilen jodmethyl und einer Auflösung von i t Gewichtsteilen Natrium in i5o Gewichtsteilen Alkohol versetzt und einige Zeit erhitzt. "Nach beendigter Reaktion wird wie in Beispiel i aufgearbeitet. -Der so erhaltene Diäthylaminoäthylhydrochinonmonomethvläther ist mit dem nach Beispiel i erhaltenen Produkt identisch.Example i 3.7 parts by weight of sodium are dissolved in 50 parts by weight of alcohol and 20 parts by weight of hydroquinone monomethyl ether and 25 parts by weight of diethylaminochloroethanol are added. The reaction begins at room temperature and is completed by heating. Then, it is poured into water, the lifted separating out 01, dried and distilled. The dieth_vlaminolithylhydroquinone monomethyl ether goes under 15mm pressure as a colorless liquid which forms readily crystallizing salts with acids which can be obtained by conventional methods. The hydrochloric acid salt z. B. crystallizes from ethyl acetate in colorless needles that melt at 121 to I22 °. Example e: 100 parts by weight of hydroquinone monodiäthvlaminoäthvläther 67 parts by weight of iodomethyl and a solution of i t parts by weight of sodium in i5o parts by weight of alcohol are added and the mixture is heated for some time. After the reaction has ended, the work-up is carried out as in Example I. The diethylaminoethylhydroquinone monomethyl ether thus obtained is identical to the product obtained in Example i.

Der in diesem Beispiel benutzte Hydrochinonmonodiäthylaminoäthyläther wird durch Kondensation von Hydrochinon mit Diäthylaminochloräthanol mittels Natriumalkoholat als dunkel gefärbtes C51 gewonnen, das sich bei der Destillation im Vakuum teilweise zersetzt.The hydroquinone monodiethylaminoethyl ether used in this example is made by condensation of hydroquinone with diethylaminochloroethanol using sodium alcoholate obtained as dark-colored C51, which is partially removed during distillation in vacuo decomposed.

Claims (1)

PATENT-ANSPRUCH. Verfahren zur Darstellung von Dialkyläthern des Hydrochinons mit einem basischen Alkylrest, dadurch gekennzeichnet, daß man auf gesättigte Monoalkyläther des Hydrochinons basische Alkylhalogenide oder auf basische Monoalkyläther dieses Phenols Alkylhalogenide bei Gegenwart alkalisch wirkender Mittel einwirken läßt.PATENT CLAIM. Process for the preparation of dialkyl ethers of hydroquinone with a basic alkyl radical, characterized in that one uses saturated monoalkyl ethers of the hydroquinone basic alkyl halides or basic monoalkyl ethers this Phenolic alkyl halides can act in the presence of alkaline agents.
DEF55139D 1923-12-18 1923-12-18 Process for the preparation of dialkyl ethers of hydroquinone with a basic alkyl radical Expired DE423037C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEF55139D DE423037C (en) 1923-12-18 1923-12-18 Process for the preparation of dialkyl ethers of hydroquinone with a basic alkyl radical

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF55139D DE423037C (en) 1923-12-18 1923-12-18 Process for the preparation of dialkyl ethers of hydroquinone with a basic alkyl radical

Publications (1)

Publication Number Publication Date
DE423037C true DE423037C (en) 1925-12-18

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Family Applications (1)

Application Number Title Priority Date Filing Date
DEF55139D Expired DE423037C (en) 1923-12-18 1923-12-18 Process for the preparation of dialkyl ethers of hydroquinone with a basic alkyl radical

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DE (1) DE423037C (en)

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