[RaInBowDaSh1488]

So this is the NMR of an alcohol that has been a bit of a mystery for me. All I am doing is reducing it from the corresponding acid which is very simple. I very rarely have any problems with impurities after I do reductions. Usually I just run the reaction to completion, do the work up and end up with what I want. Worst case I can't get it to go to completion and I just use a column to remove unreacted material.

The compound in question is 3,3-diphenylpropanol. I will link the structure for anyone who doesn't want to look it up or think about what it looks like.

I've run this reaction quite a few times and keep ending up with almost exactly the spectra I have provided. Granted this is unfortunately the worst spectra I have. The shimming on this one is quite bad, but I think it gets the point across.

Anyway, I am fairly certain the peak at ~4.2ppm is the proton nearest the two phenyl groups. It looks about right and integrates right. The signals around ~3.7 and ~2.3 are so weird though. I always end up getting extra sets of peaks where it would seem I should only have one. Also the broad singlet at ~1.7 is transient between spectra, possibly the alcohol proton?

I can't seem to get away from these extra peaks. Previously I thought they were impurities, but now I am starting to think they may not be. I am having a hard time telling if they are coupled to what I think are the peaks of my product.

Any help or advice would be appreciated!


Link to spectra:
http://imgur.com/6O777QA