Sciencemadness Discussion Board
Not logged in [Login ]
Go To Bottom

Printable Version  
 Pages:  1    3
Author: Subject: How to selectively alkylate an aromatic ring?
Maui3
Hazard to Others
***




Posts: 134
Registered: 9-9-2024
Member Is Offline


[*] posted on 3-2-2025 at 03:15


Niklas, if you can't find an alternative to the TiCl4, maybe we could go back to this way of making it:

I will buy some sodium anyway for this.
I don't have or want to own hexavalent chromium compounds, but I will buy some potassium permanganate, if that can be used.
And I have some hydrazine.
I just don't have the HgO, and TMSCl seems very expensive.

The reason I choose the other route first was because it was quite short.. but no worries if we can't find a cheap and accesable alternative to TiCl4.
View user's profile View All Posts By User
Niklas
Hazard to Self
**




Posts: 71
Registered: 1-12-2023
Location: Germany
Member Is Offline

Mood: Polymerized

[*] posted on 3-2-2025 at 11:15


One last idea I would have I somehow forgot about before would be to make isoamylbromide, and then try alkylating acetylene with it using something like sodium amide as the base and maybe ethylene diamine as the solvent (suggesting this rather odd solvent choice as alkylations of acetylene are typically done in liquid ammonia, and just like it’s fine to use EDA for Birch-reactions I guess it may work here as well).
View user's profile View All Posts By User
Maui3
Hazard to Others
***




Posts: 134
Registered: 9-9-2024
Member Is Offline


[*] posted on 3-2-2025 at 11:38


Thanks!

It is a good idea, but I think it is a bit difficult for me too. I looked at some threads on here, and found that the TiCl4 can be made.. somewhat easily. So I think I'll try that.

Thank you for your help! I hope it's okay that I update you guys on my synthesis on here.
View user's profile View All Posts By User
Niklas
Hazard to Self
**




Posts: 71
Registered: 1-12-2023
Location: Germany
Member Is Offline

Mood: Polymerized

[*] posted on 3-2-2025 at 13:11


Yeah of course!
Yeah simply making TiCl4 is ofc the other option (Thyzoid should have a video on it), I recommend complexing it with THF right after making as the resulting adduct is a lot less sensitive and just generally nicer to handle, and still works perfectly fine for McMurry reactions (as you generally us THF as the solvent it gets formed in-situ either way).
View user's profile View All Posts By User
Maui3
Hazard to Others
***




Posts: 134
Registered: 9-9-2024
Member Is Offline


[*] posted on 4-2-2025 at 09:35


Thank you for Niklas! Will do!
View user's profile View All Posts By User
 Pages:  1    3

  Go To Top