[Messi]

OK, that's clear now.
Try a test reaction on that dark red oil.
Have you run an NMR, what is the yield, assuming that's your product?

Yes, just did a test reaction... let's see what I get. Theoretically speaking, I should get some nice white crystals, no?

Yes, I had ran an NMR of prolinol, I got the spectra shown below.

[discodermolide]

If you get nice white crystals from that dark red oil then I will be pleased.
The prolinol looks ok. Did you run a NMR of the dark red oil? If not do so while you are waiting.

[Messi]

If you get nice white crystals from that dark red oil then I will be pleased.

No crystals what so ever.



I just took NMR of my oil shown below:

[discodermolide]

So things changed. Try and analyse both the spectra.

[Messi]

So things changed. Try and analyse both the spectra.

Well technically things should have changed, no? I add HBr so my amine gets protonated and maybe some HBr might replace my hydroxyl in prolinol (Br replaces OH).

This is so odd! Not sure what I should do now...

[discodermolide]

That could have happened.
Try and purify a bit of your red oil. I think the method used iso-propanol?

[Messi]

That could have happened.
Try and purify a bit of your red oil. I think the method used iso-propanol?

The thing I'm confused about is that I thought whenever an amine is protonated with an acid like HBr it switches to salt form. I have no idea why this is not happening here!

[discodermolide]

It does form the HBr salt. Just try and crystallise it.

[Messi]

It does form the HBr salt. Just try and crystallise it.

I read this somewhere:

One caveat that I noticed in my lab days long ago is that
hydrohalide salts will clump out in an oily mass if the
gas or the amine solution is the slightest bit wet.

Is this what is perhaps happening?

[discodermolide]

That could be.
Add a bit of anhydrous sodium sulphate shake and filter it.
Remove the isopropanol and try the crystallisation again.
It does not look so red now, a nice yellow gum.
Remember do not add too much Iso-propanol for the crystallisation, start with a small quantity warm it up and add more until the solid dissolves, then cool it slowly.

[Messi]

That could be.
Add a bit of anhydrous sodium sulphate shake and filter it.
Remove the isopropanol and try the crystallisation again.
It does not look so red now, a nice yellow gum.
Remember do not add too much Iso-propanol for the crystallisation, start with a small quantity warm it up and add more until the solid dissolves, then cool it slowly.

Should I do this before adding my PBr₃?

[discodermolide]

Yes.
How is the test reaction looking?

[Messi]

Yes.
How is the test reaction looking?

Unfortunately not very well. I am not sure if I am mixing up my steps or what is going on. I don't know what to say...

[discodermolide]

Yes.
How is the test reaction looking?

Unfortunately not very well. I am not sure if I am mixing up my steps or what is going on. I don't know what to say...

What is happening?

[Messi]

It simply isn't crystalizing! I think I am going to get some food and come back to the lab with a fresh mind.