I'm interested in working with an amine-based (N2228Cl)-based cellulose-solvent that can be diluted with DMAc, acetone(!) and pyridne with remaining cellulose dissolving capacity. And I have chosen to think about using pyride (DMAC is very toxic and acetone volatile)
However, to create cellulose derivatives I need to deprotonate the cellulose and for this I need a strong base.
Now MeOH are all insoluble in pyridine. I found that also NaOC2H5 and KC(CH3)3 also are.
I found the chemical NaOC(CH3)2C2H5 (Sodium tert-pentoxide, see link) that seem possible to dissolve.
I do not want to use LiH or LiBu or any other VERY strong bases since they will cause unwanted side reactions.
Should I use this chemical or do you have any other suggestions.
What's the approximate pKa of your cellulose at the site of deprotonation?
How about LDA?
Enolate could be a base if no side reaction from substitution.
Cellulose has pKas of 12.5-14 (approximately). Enolates seem to reactive (I'm sorry to say), What does LDA stand for?
LDA stand for lithium diisopropylamide, a rather stong base.
If enolates are too reactive (pKa around 20), then I think alkoxides are the only choice, and probably need excess to push the equilibrium.
By the way, do you mean MeOH and pyridine are not miscible? Seems very unlikely.
MeOH and pyridene is miscable if you say so but I can't get NaOC2H5 to dissolve in pyridine,
Thanks for the answer! :-)
2,6-di-tert-butylphenol has pKa around 17 in MeOH. (Trans. Faraday Soc., 1970,66, 1348-1350)
You may prepare the corresponding phenoxide for trial.
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