Production of an in situ solution was explored first (Figure ). A solvent swap to toluene was desired as toluene could be used in the ensuing synthetic chemistry. In first attempts toward this goal, epichlorohydrin was directly distilled from the reaction mixture under vacuum, and then toluene was added intermittently to make-up the volume lost from epichlorohydrin evaporation. Volatiles were then fully removed to give a glycidyl pivalate residue. The process was repeated three times. This led to a loss of active glycidyl pivalate in solution as observed by decrease in the assay strength (10-15%) and also the observation of unidentified by-products (Figure ). Again, heat and concentration sensitivities were suspected to cause the loss in activity. If the solvent swap could be conducted while maintaining constant volume, perhaps the decomposition could be avoided. This was accomplished by adding toluene continuously to a stirred solution of the glycidyl pivalate reaction mixture which was under vacuum (Figure ). Performing the solvent swap in this manner largely prevented the loss of active glycidyl pivalate to decomposition products. The reaction mixture had a 94% AY at the end of reaction (EOR) and a 90% AY after removal of epichlorohydrin through a toluene solvent swap. This yields a reactive solution which could be used for the subsequent alkylation step. 2b Next, we attempted to isolate glycidyl pivalate in good purity by direct distillation 9 (Table ). First, sodium chloride was removed from the reaction mixture via filtration, and then epichlorohydrin was evaporated from the filtrate. Care was taken to evaporate epichlorohydrin at minimal temperature under strong vacuum (<10 torr) so that vapors of epichlorohydrin do not exceed 60 °C. After evaporation, the assay yield of the crude glycidyl pivalate residue was 87%.