In this paper, the cheap and easily available 1, 8-dihydroxyanthraquinone and 1, 4-dihydroxyanthraquinone were used as starting materials, and different routes were designed to prepare the key intermediate product 1, 8, 13, 16-tetrahydroxytriptycene. and 1, 4, 5, 8-tetrahydroxytriptycene, and then esterified with trifluoromethanesulfonic anhydride to obtain 1, 8, 13, 16-tetra[(trifluoromethanesulfonyl)oxy]triptycene and 1, 4, 13, 16-tetra[(trifluoromethanesulfonyl)oxy]triptycene,the yields were 46.2% and 70.5%, respectively. The structure of the products were characterized by ESI-HMS and NMR (1H NMR, 19F NMR). The synthesis method is simple, efficient, and the intermediate products are stable, which can provide a reference for the industrialized production of the aryl trifluoromethanesulfonate with triptycene as the skeleton.