Catalytic transformation of 1-Adamantanol has been carried out over microporous materials viz. Zeolite-Y, USY, Beta, Mordenite, SAPO-8, SAPO-5, and CoAPO-5 whose pore size is close to the kinetic diameter of the reactant and product molecules. In presence of chloroacetic acid solvent, 1-adamantanol (1-Adol) forms 1-adamantylacetate (1-Adoac) and equilibrium is established between 1-Adol and formed 1-Adoac thereby reduces polymerization of 1-Adol to some extent. The products formed are 2-Adamantane derivatives (2-Derivatives) viz., 2-Adamantanol (2-Adol), 2-Adamantanone (2-Ado) and 2-Adamantane acetate (2-Adoac) which serve as important intermediates for a variety of pharmaceuticals and functional materials, along with adamantane and some of polymerized products. 2-Ado is produced via disproportionation of 1-Adol and formed 2-Adol attributed to an intermolecular hydride transfer reaction over solid acid catalysts. Acidity plays an important role in producing 2-Derivatives selectively. Influence of pore size on the transformation of 1-adamantanol has also been discussed. A new experimental strategy along with addition of adamantane with the reactant, reduces the formation of least preferred adamantane from 1-Adol, and in turn, increases the selective formation of more favored 2-Derivatives. The formation of products through a different route has been completely explained with the assistance of a detailed reaction mechanism.