Sciencemadness Discussion Board

Synthesis of CAS 3179-63-3 or 3-Dimethylaminopropan-1-ol

Kloberth - 29-7-2023 at 12:06

I am trying to make this compound for a bigger synthesis I plan to do but I just cannot find any information on the synthesis of it. Most likely I am just not good at searching. So please help if someone can find a more detailed explanation as the one on german wikipedia:

https://de.m.wikipedia.org/wiki/3-Dimethylaminopropanol:

"3-Dimethylaminopropanol kann durch wasserfreies Kochen von Dimethylamin und Allylalkohol mit Natriumhydroxid-Flocken und anschließender wässriger Aufarbeitung synthetisiert werden.[3] Das Produkt kann bei dieser Syntheseroute mit Benzol aus der wässrigen Reaktionslösung extrahiert werden."

"3-Dimethylaminopropanol can be synthesised by waterfree "cooking" of Dimethylamine and Allyl alcohol in sodium hydroxide. Then work up with water and extraction with benezen."

There is also a reaction scheme which shows themperatures ao 115-120°C which is a questionmark for me. Should this be dobe under pressure??

Can someone can dig up a halfdetailed synthesis of this compount?

Tsjerk - 29-7-2023 at 13:13

What bigger plan? I can imagine some bigger plan this compound could be used for, but not really one this compound is really necessary for.

Fery - 29-7-2023 at 21:18

https://sci-hub.ee/10.1021/ja01158a026
Quote:
A mixture of 45 g. (1 mole) of
dimethylamine, 116.1 g. (2 mol) of allyl alcohol (Shell Chemical Co.) and 42 g. of flake sodium hydroxide (96-98%) was placed in an autoclave and heated with agitation at 115-120' for twenty hours. The reaction mixture
was cooled to 35-40', the semi-solid mass was dissolved
in 200 cc. of water, the layers were separated and the
aqueous layer was extracted with three 50cc. portions of
benzene. The combined alcohol layer and extracts were dried over potassium carbonate and fractionated; b. p.
112-113 ' (150 mm.) and 162-163 under atmospheric
pressure, yield, 59-65%

Kloberth - 29-7-2023 at 21:51

I am trying to synthesise an ester with this alcohol.

Finally at least some information on the synthesis, thanks.

[Edited on 30-7-2023 by Kloberth]

Fery - 30-7-2023 at 10:56

The info is in the link you posted (DOI).

Kloberth - 30-7-2023 at 22:12

Omg I completely forgot that wikipedia lists the sources below.