DE1269135B - Process for the preparation of dialkylaminoalkyl ethers of polyhydric phenols - Google Patents

Description

FEDERAL REPUBLIC OF GERMANY

GERMAN

PATENT OFFICE

EDITORIAL

Int. CL:

German class:

Number:
File number:
Registration date:
Display day:

C07c

A61k

12 q- 32/01
30 h-2/36

P 12 69 135.9-42
April 6, 1963
May 30, 1968

The present invention relates to a process for the preparation of Dialkylaminoalkyläthern of polyhydric phenols by condensation of the alkali metal salts of polyhydric phenols with water-soluble salts of tertiary Alkylaminoalkylhalogenide, which is characterized in that the reaction is carried out as a solvent at a temperature below 6O ⁰ C in the presence of alkali and water. Some of these preparations are characterized by curare effects.

It is already known to produce basic substituted phenol ethers from polyhydric phenols by the latter in an anhydrous organic solvent, e.g. B. toluene, reacted with sodium amide and then with halogenated tertiary amines at boiling point (U.S. Patent 2,544,076) treated.

The previously known method has the disadvantage that it is higher temperatures, combustible organic Solvents, long reaction times and relatively cumbersome work-up, i.e. greater expenditure of time, requires.

It has now been found that dialkylaminoalkyl ethers of polyhydric phenols can be prepared in a simpler manner and with very good yield even at room temperature if water is used instead of the organic solvent. According to the invention, an aqueous solution of caustic alkali is mixed with a polyhydric phenol, e.g. B. pyrogallol, and a concentrated solution of dialkylaminoalkylchloride hydrochloride in water at room temperature is added dropwise to the resulting phenolate solution while stirring. As a result of the formation of two mutually insoluble phases, the mixture becomes cloudy after a while. The stirring at room temperature for a time continues and can then optionally heat, to complete the reaction, slowly to 50 to 6O ⁰ C, it has become clear until the settling upper oily layer, and can be separated well.

The basic phenol ether, which is not very colored in this way, is characterized by the applied mild reaction conditions are characterized by high purity. It can be quaternized in the usual way will.

example

A solution of 12.6 g of pyrogallol and 26.4 g of caustic soda in 50 cm ^{3 of} water is added with thorough stirring for the preparation process
of dialkylaminoalkyl ethers
of polyhydric phenols

Applicant:

VEB German Hydrogenation Plant Rodleben,

Rodleben near Roßlau / Elbe

Named as inventor:

Dr Heinz-Joachim Engelbrecht f, Dessau

at 20 ° C within one hour a solution of

ao 59 g of diethylaminoethyl chloride hydrochloride added ^{dropwise to 29 cm 3 of} water. The mixture is then stirred for hour at 20 ⁰ C, then slowly heated to 6O ⁰ C and maintained there for an additional hour at the same temperature. After diluting

As with 50 cm ^{3 of} water, the oil layer formed is separated off in a separating funnel and dried over potassium carbonate. After separating off the desiccant, 30 g of 2,3-tris (| S-diethylaminoethoxy) benzene corresponding to 70.9% of theory are obtained. The base is distilled under vacuum (Kp.q _(1175-178 ⁰ C) and then transferred in a conventional manner by heating with ethyl iodide in an alcoholic solution in the Trisäthojodid. Yield 82.3% of theory. After recrystallization from a mixture of Alcohol and acetone have a melting point of 238 to 24O ⁰ C.

Claims (1)

Claim: Process for the preparation of dialkylaminoalkyl ethers of polyhydric phenols by condensation of the alkali salts of polyhydric phenols with water-soluble salts of tertiary alkylaminoalkyl halides, characterized in that the reaction is carried out in the presence of alkali and water as solvent at temperatures below 60 ^° C.