[Nokovi]

I'm searching for effective methods of tosylating a the alcohol of ricinoleic acid, having difficulty finding methods in the literature with high yields for 2ndary long chain alcohols like the above.
I was wondering if anyone could give me any advice with running tosylations like this?
Not necessarily looking for answers or a synthesis route, just some advice or pointers for guidance.
Any help would be much appreciated!

[Archer]

You could try deprotonation with a strong non-neucleophilic base at low temperature for a few hours prior to adding the tosyl chloride.

I have had success using stoichiometric KH in dry THF in a dry-ice / acetone bath for 8 hours prior to adding the electrophile and allowing the reaction to return to room temperature. This works for secondary alcohols in the presence of a secondary amine.

[Nokovi]

What about using some larger more hindered base than KH, (trying to use readily available, cheap and safe reagents where possible) for the deprotonation?
I've been looking into pKa/pKb tables for possible reagents, I'd hopefully like to be able to use Et3N in a suitable solvent, to cut down on waste and use fewer solvents, though haven't had enough time to read through things properly yet.