I am attempting a synthesis for acetylacetone. The preparation I wish to carry out is described on orgsynth by condensation of acetone and ethyl acetate with a base catalyst.
The problem for me is that I only have $\ce{t-BuOK}$, no THF and $\ce{t-BuOH}$ in sight, only $\ce{EtOH}$. First I searched for solubility of $\ce{t-BuOK}$ in ethanol, only to find nothing. It gave me some ideas why there is no data for the solubility so I assumed already that they react (Why didn't I think of this in the first place). I instantly looked up for this procedure but I could not find anything satisfactory for this specific reaction, only patents about metathesis reactions of alkoxides with higher carbon chain alcohols. On the Wikipedia site there is a line of information that was somewhat useful, which states that "many alkoxides are prepared by salt metathesis from sodium ethoxide", but still not satisfactory since its the reverse what I am looking for.
The $\mathrm{p}K_\mathrm{a}$ of $\ce{EtOH}$ is 15.9 while $\mathrm{p}K_\mathrm{a}$ of $\ce{t-BuOH}$ is 16.5 in water. Looking at the values in DMSO the value of $\ce{EtOH}$ is still lower, so perhaps it can be generally stated the ethanol molecule has more tendency to deprotonate. Assuming and without cited literature by using excess $\ce{EtOH}$ (and as a solvent of course) I am expecting them to produce $\ce{EtOK}$ and $\ce{t-BuOH}$ by equilibration the mixture. I think that which base I use does not really matter in the reaction, but I'm short of solvents for solving $\ce{t-BuOK}$ efficiently and a little tertiary alcohol wont mess up my experiment. I am very confident about this simple metathesis reaction, but I would like to hear your ideas too before doing anything.
So my question, in short is the following: Will $\ce{t-BuOK}$ react with $\ce{EtOH}$ to produce $\ce{EtOK}$ and $\ce{t-BuOH}$?
I am of course aware of the dangers of these compounds, and have a basic experience in doing simple preparations like these.