[Nekromantis]

Hi,
I have a problem. I would like transform hydroxyl group to NH2 in menthol. I found simple method (anyway I thought so).

A New Novel and Practical One Pot Methodology for Conversion of Alcohols to Amines
Communication of Synthetic Organic Chemistry, 30:12, 2233-2237, DOI:10.1080/00397910008087402

The scientists received the product in 88% yield. I made this reaction a few times and I have nothing. After concentration I have a solid what precipitate looks like triphenylphosphine... NMR analysis showed that it is PPh3. Do you have any ideas what is wrong?

[Dan]

Can you describe exactly what you did?

It might be worth running the reaction with 1 equiv PPh₃ and trying to isolate the azide first to confirm that the first step works.

Alternatively, could use DPPA (diphenylphosphoryl azide), which would avoid heating NaN3.

[Nekromantis]

I make exactly what is described in publication. I prepared mixture od CCl4 and DMF. I added menthol, sodium azide and the last PPh3. The mixture was stirred and heated by 24 hours. When mixture is cold I added 5 ml water and stirred about 5 minutes. I moved all in separatory funnel and extracted diethyl ether. Organic layer was washed with water and placed in freezer. Some crystals was precipitated and I fliltared off. I dried the ether and remove in rotary evaporation.

Like I descriped before i have some solid state. NMR spectra showed only PPh3...

[rolnor]

You get PPh3O as byproduct, maby this is what you isolate. A good thing to do would be to monitor the reaction, with TLC, GC or other method.