(Hydroxy)cinnamic acids (HCAs), a kind of prevalent phenolic acid compound, boast diverse biological activities. However, their limited liposolubility impedes their utilization in oil-based systems. Addressing this challenge, we presented an eco-friendly approach to synthesize (hydroxy)cinnamic monoterpenyl esters in biomass solvent 2-methyltetrahydrofuran (2-MeTHF), grafting antibacterially active monoterpenyl onto phenolic acid compounds through esterification/transesterification. This green enzymatic catalytic strategy successfully synthesized a series of cinnamic monoterpenyl esters (yield >87.84%), p-coumaric monoterpenyl esters (yield >67.26%), and caffeic monoterpenyl esters (yield >10.55%). The mechanism difference in reaction efficiency of different hydroxyl cinnamic acids was revealed through kinetic calculation and molecular docking. As the number of hydroxyl group increased, the affinity between substrates and lipase decreased, which was reflected by the Km value, in which the Km value of cinnamic acid, p-coumaric acid and caffeic acid were 23.72, 52.04 and 60.05, respectively. Furthermore, molecular docking results showed that the strong binding of the hydroxyl groups to the hydrophobic cavity of the lipase resulted in the need for more energy to twist the reaction site closer to the active center during the reaction. This research provided a green and feasible route for the synthesis of phenolic acid ester derivatives.