The Hive > Serious Chemistry

First published direct reduction of COOH to CH3

<< < (3/5) > >>

Rhodium:
The purpose of the sodium hydride (NaH) is the same as for NaOH, to deprotonate the OH groups on the aromatic ring. NaH does this more effectively and irreversibly than NaOH, as the reaction with sodium hydride goes PhOH + NaH => H2 + PhONa, while with hydroxide water is formed, and the reaction is reversible.
https://www.rhodium.ws

superhybrid:
I guess one other problem would be the DCM connecting with the amine group. What would happen if one would say acetylate the amine as a protecting group. This would possibly disallow cojugation with the amine from the mono chloro intermediate.

Dope_Amine:
I hope anybody thinking of trying this reaction realizes just how dangerous HF is!
something for your mind.......

Alphabeta121:
if you reacted 1 equiv. of DCM with the deprotonated dopamine, my assumption would be that it would methylenedioxy-ate before it alkylated the amine.
but you know what happens when one assumes...
alphabet

obituary:
as the alkylation is potentially reversible, you're probably right, once that ring is formed, it's not coming back undone- the ionic salt formed is going to stay that way

Navigation

[0] Message Index

[#] Next page

[*] Previous page