AT104012B - Process for the preparation of saturated dialkyl ethers of hydroquinone with a basic alkyl radical. - Google Patents
Process for the preparation of saturated dialkyl ethers of hydroquinone with a basic alkyl radical.Info
- Publication number
- AT104012B AT104012B AT104012DA AT104012B AT 104012 B AT104012 B AT 104012B AT 104012D A AT104012D A AT 104012DA AT 104012 B AT104012 B AT 104012B
- Authority
- AT
- Austria
- Prior art keywords
- hydroquinone
- preparation
- alkyl radical
- basic
- dialkyl ethers
- Prior art date
Links
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
<Desc/Clms Page number 1>
Verfahren zur Darstellung von gesättigten Dialkyläthern des Hydrochinons mit einem basischen Alkylrest.
Es wurde gefunden, dass Dialkyläther des Hydrochinons mit einem basischen Alkylrest und ohne ungesättigte Substituenten im Kern hervorragende physiologische Eigenschaften zeigen. Die neuen Körper haben sich als besonders wirksam erwiesen bei gewissen Erkrankungen des Herzens. Sie wirken blutdruckherabsetzend, verlangsamern den Puls und übertreffen in dieser Hinsicht die analogen o-oder m-substituierten Verbindungen. Man kann sie in glatter Reaktion mit vorzüglicher Ausbeute in der Weise darstellen, dass man auf gesättigte Monoalkyläther des Hydrochinons basische Alkylhalogenide oder auf basische Monoalkyläther des Hydrochinons Alkylhalogenide, zweckmässig bei Gegenwart alkalisch wirkender Mittel, einwirken lässt.
Beispiel l : 3-7 Gewichtsteile Natrium werden in 50 Gewichtsteilen Alkohol aufgelöst und mit 20 Gewichtsteilen Hydrochinonmonomethyläther und 25 Gewichtsteilen Diäthylaminochloräthanol versetzt. Die Reaktion beginnt schon bei Zimmertemperatur und wird durch Erwärmen vervollständigt.
Dann wird in Wasser gegossen, das sich abscheidende Öl abgehoben, getrocknet und destilliert.
EMI1.1
EMI1.2
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werden mit 67 Gewichtsteilen Jodmethyl und einer Auflösung von 11 Gewichtsteilen Natrium in 150 Gewichtsteilen Alkohol versetzt und einige Zeit erhitzt. Nach beendigter Reaktion wird wie in Beispiel 1 aufgearbeitet.
Der so erhaltene Diäthylaminoäthylhydrochinonmethyläther ist mit dem nach Beispiel 1 erhaltenen Produkt identisch.
Der in diesem Beispiel benutzte Hydrochinonmonodiäthylaminoäthyläther wird durch Kondensation von Hydrochinon mit Diäthylaminochloräthanol mittels Natriumalkoholat als dunkel gefärbtes Öl gewonnen, das sich bei der. Destillation im Vakuum teilweise zersetzt.
**WARNUNG** Ende DESC Feld kannt Anfang CLMS uberlappen**.
<Desc / Clms Page number 1>
Process for the preparation of saturated dialkyl ethers of hydroquinone with a basic alkyl radical.
It has been found that dialkyl ethers of hydroquinone with a basic alkyl radical and without unsaturated substituents in the nucleus show excellent physiological properties. The new bodies have been shown to be particularly effective in treating certain heart diseases. They have a blood pressure lowering effect, slow the pulse and in this respect outperform the analogous o- or m-substituted compounds. They can be prepared in a smooth reaction with excellent yields by allowing basic alkyl halides to act on saturated monoalkyl ethers of hydroquinone or on basic monoalkyl ethers of hydroquinone alkyl halides, expediently in the presence of alkaline agents.
Example 1: 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 oil that separates is lifted off, dried and distilled.
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67 parts by weight of iodomethyl and a solution of 11 parts by weight of sodium in 150 parts by weight of alcohol are added and the mixture is heated for some time. After the reaction has ended, work-up is carried out as in Example 1.
The diethylaminoethylhydroquinone methyl ether thus obtained is identical to the product obtained according to Example 1.
The hydroquinone monodiethylaminoethyl ether used in this example is obtained as a dark colored oil by condensation of hydroquinone with diethylaminochloroethanol using sodium alcoholate. Partly decomposed by distillation in vacuo.
** WARNING ** End of DESC field may overlap beginning of CLMS **.
Claims (1)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AT104012T | 1925-02-04 |
Publications (1)
Publication Number | Publication Date |
---|---|
AT104012B true AT104012B (en) | 1926-08-25 |
Family
ID=3622094
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
AT104012D AT104012B (en) | 1925-02-04 | 1925-02-04 | Process for the preparation of saturated dialkyl ethers of hydroquinone with a basic alkyl radical. |
Country Status (1)
Country | Link |
---|---|
AT (1) | AT104012B (en) |
-
1925
- 1925-02-04 AT AT104012D patent/AT104012B/en active
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