The very useful organic solvent 2-octanol is widely employed in the industry, and the direct hydration of olefins is an important method for its production. However, a slow transfer rate during a reaction due to the poor mutual solubility of the reactants is a problem; a cosolvent can be used to solve it. In this study, the feasibility of using the direct hydration of 1-octene via a catalytic distillation process using 1,4-dioxane as a cosolvent was investigated. First, the COSMOtherm program was used to identify and screen many typical cosolvents. Subsequently, the kinetics of the direct hydration reaction of 1-octene using 1,4-dioxane as a cosolvent and an HZSM-5 molecular sieve as the catalyst were determined experimentally. Finally, kinetic and thermodynamic models were utilized to create non-reactive and reactive residual curve maps to assess the feasibility of proceeding with the reaction. Applying a suitable Damköhler number (Da) value and the residual curve changes demonstrated that proceeding with the process was reasonable and feasible. For 0 < Da < 0.03, the reaction kinetics drove the process and 2-octanol was produced via a reaction distillation column procedure. Lastly, two conceptual design processes for the synthesis process of 2-octanol catalytic distillation were proposed and the related analysis carried out.