Abstract Evaluating stereolability of target chiral chemical is pivotal when developing enantioselective studies. Ethofumesate‐2‐hydroxy is one of the main metabolites of ethofumesate, a chiral herbicide currently marketed as racemate. In order to perform enantioselective pharmacokinetic and metabolism studies, the stereolability of susceptible molecules should be evaluated. Based on that, dynamic high‐performance liquid chromatography experiments were performed to evaluate ethofumesate‐2‐hydroxy enantiomerization process on‐column. The thermodynamic results helped understand that ethofumesate‐2‐hydroxy enantiomerization is a bimolecular process assisted by acid and base catalysis. The enantiomerization barrier determined suggested that ethofumesate‐2‐hydroxy single enantiomers may undergo extensive racemization at ambient temperature turning ethofumesate‐2‐hydroxy enantioselective studies into an unfeasible task.