Technical Abstract: We have studied the reaction selectivities of acid catalyzed ring opening reactions of epoxidized methyl oleate (methyl 9,10-epoxy stearate; EMO), to form either acetal or branched ester products. We have produced: methyl 9-(2-butyl-2-methyl-5-octyl-1,3-dioxolan-4-yl) nonanoate (hexanone methyl stearate acetal, HMSA), an oleochemically based acetal, in 83% isolated yield; from epoxidized methyl oleate and 2-hexanone. Utilizing our reaction chemistry, we have also been able to demonstrate the relative selectivities in competitive experiments by reacting EMO with 2-pentanone and octanoic acid. Finally, by controlling temperature and acid concentration, we were able to control the product distribution of the reaction of EMO with the bi-functional levulinic acid. We could favor either the acetal, or branched ester product in this work. This research may help lead to the formation of new hydrophobic molecules for the synthesis of new surfactants from oleochemicals.