Using cis-1, 2-cyclohexanedicarboxylic anhydride as raw material, trans-1, 2-cyclohexanedicarboxylic acid was obtained by cis-trans isomerization, then, (1R, 2R)-(-)-cyclohexanedicarboxylic acid was prepared via a two-step process of the chemical resolution and acidification by employing R-(+)-alpha-methylbenzylamine as resolving agent. The effects of the reaction conditions, including the type of catalyst, reaction temperature and reaction time, on the content of trans-1, 2-cyclohexanedicarboxylic acid were investigated, and the effects of the type and amount of solvent on the chiral resolution were also studied. The results show that the optimal reaction conditions of the synthesis of trans-1, 2-cyclohexanedicarboxylic acid were found as follows: sulfuric acid as reaction catalyst, the reaction temperature was maintained above 120 °C and the optimal reaction time was 12 h. The yield of trans-1, 2-cyclohexanedicarboxylic acid was approximately 80% under such optimal conditions. Detected by 1H NMR, the content of trans-1, 2-cyclohexanedicarboxylic acid was 99.3%. Using R-(+)-alpha-methyl benzylamine as resolving agent, the yield of (1R, 2R)-(-)-cyclohexanedicarboxylic acid ammonium salt was approximately 38%. The reaction conditions have been optimized as follows: anhydrous methanol as the reaction solvent, n (trans-1, 2-cyclohexanedicarboxylic acid) ∶ n (R-(+)-alpha-methyl benzylamine) = 1 ∶ 1, and W (trans-1, 2-cyclohexane dicarboxylic acid) ∶ V (methanol) = 1 ∶ 3. Detected by chiral HPLC, the ee value of the target compound was 98.48%.