[wonka_vision]

Hi - I'm trying to form a ketal containing amine through the following reaction:



To drive the reaction I have been slowly adding concentrated NaOH (in water) under reflux for 24 hours. I then extract with dichloromethane in order to get a yellow oil. The problem is that I often don't get a product (it's only worked a couple of times for me out of the many times I've done this reaction). Can someone think of a reason why I could be losing my product?

Thanks

Mod edit: img tags added. Dan

[kriggy]

Isnt the product usualy obtained by use of hydrazine?

[wonka_vision]

It is, but I had a really difficult time with separation last time I used hydrazine. I'm actually in a chemical engineering department, so our access to equipment is lacking.

[phth]

The rxn is competing to form phthalamide+ROH.  You could just put NaN₃+RX and then reduce N₃ to NH₂ by commmon hydrogenation catalysts(e.g. Pd/C wont react with ether--> http://www.organic-chemistry.org/synthesis/N1H/reductionsazides.shtm) or PPh₃ http://www.organic-chemistry.org/namedreactions/staudinger-reaction.shtm  May also work better to convert it to a dithioketal which is less sensitive than ketals and can be removed with reagents such as PhI(OAc)₂ if your goal is not just the exact chemical in your .png