J.R. S. answered 09/20/17
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There are several possible reasons for a low recovery upon recrystallization. Some are
(a) Choice of incorrect solvent. If the compound of interest has low solubility at all temperatures, or high solubility at all temperatures, the recovery will be low.
(b) Volume of solvent. If too much solvent is used, it will be difficult to obtain sufficient yield of crystals and yield will be lwo.
(c) Time. Not enough time was allowed for all of the crystals to form. Crystallization is a time-dependent process.
(d) Technique. Recrystallization is sort of an art, more than a science. There are certain techniques that improve yield, such as using ice-water bath to initiate the process and then changing the temperature, or seeding, etc.