[kriggy]

Hi there,
how many equivalents of hydroxide is required for basic amide hydrolysis? I wrongly calculated the mass of hydroxide and have added only 3 equivalents instead of 9 as the procedure wanted. Im just thinking if it will run  into complete deprotection or not. Is it possible that it will complete but at slower rate?
Thanks

[TheUnassuming]

In theory it should be fine, just slower perhaps.

[orgopete]

It depends. The intermediate is a dianion. If three equivalent instead of nine but 1/3 volume, may not be as bad, but if you have diluted the solution, I think you may greatly slow the reaction as it will become more difficult to form the needed dianion.

[kriggy]

Thanks. It wenr OK however after 20 hrs there are still traces of starting material so I did it again with the correct amount of hydroxide and it went to full deprotection after about 3,5 hours while forming maybe 1-3% of side product which I can get rid of in next steps.

PS: While refluxing hydroxide dont forget to use some silica oil or fat or whaterver you are using in a lab on glass joints. Otherwise, it will melt the joints together. And its embarassing when it happens. (At least I got cool new piece of glasware  )

[TheUnassuming]

PS: While refluxing hydroxide dont forget to use some silica oil or fat or whaterver you are using in a lab on glass joints. It will melt the joints together. And its embarassing when it happens. (At least I got cool new piece of glasware  )

haha... I hadn't even thought about that.  Live and learn I suppose .