[Rishi]

I am trying to make a few tert-butyl esters. In presence of acids, the tert-Butanol readily converts to Isobutene gas and thus resulting in loss of tert-Butanol from the reaction mixture. The only alternative that works is carrying out the reaction with the acid chloride in presence of a base as a scavanger for the liberated HCl. But that is a tedious process.
Are there any catalysts apart from sulfuric acid and PTSA that might help in the reaction without converting the tert-Butanol to Isobutene ?

[sjb]

Maybe have a look at Org Synth, Organic Syntheses, Vol. 81, p.178 (2005), or http://dx.doi.org/10.1016/j.tetlet.2006.03.005 , or similar?

[Rishi]

Did go through it. Thanks. Will try it out.

[Rishi]

IS IT POSSIBLE TO SYNTHESIZE tert-BUTYL CHLORIDE FROM tert-BUTANOL IN GOOD YIELDS ? CAN SOMEONE KINDLY SUGGEST A PROCESS WITH GOOD YIELDS ?

[James Newby]

This is a forum primarily designed to help students with their problems.  If you are after a speicific reaction it would be better to try looking on scifinder and reading some journals that have published the reaction you are looking for.

[sjb]

Well, there's http://orgsynth.org/orgsyn/orgsyn/prepContent.asp?prep=cv1p0144 for starters.

[g-bones]

what about tBuOH and SOCl2 ?

[nj_bartel]

thionyl chloride on alcohols works through an sn2 mechanism, so no that won't work.

[kiwi]

thionyl chloride on alcohols works through an sn2 mechanism, so no that won't work.

Indeed it does. But that is not what is going on here:

RCOOH + SOCl2 -> ROCl
ROCl + tBuOH -> ROOtBu

[nj_bartel]

sounded to me like bones wanted to treat the tert-butanol with the thionyl chloride 

[Rishi]

SOCl2 is quite possible but with heavy yield losses. And it might be mainly due to the acidic pH that forces the dehydration of tert-butanol to form butene gas.