Herein, we report the synthesis and characterization of four novel fullerene C60 derivatives. The carbon cage of these C60 derivatives is decorated with one or two dodecyl or triethylene glycol tails, through the appropriately modified ortho‐xyleno bridge, by utilizing the Diels‐Alder reaction of C60 with the corresponding especially designed, novel, in situ‐prepared ortho‐quinodimethanes. Two different synthetic approaches were designed and followed for the preparation of these adducts. All fullerene derivatives were characterized via 1H‐ and 13C‐NMR, matrix‐assisted laser desorption‐ionization mass spectrometry, as well as, by FT‐IR and UV‐Vis spectroscopies and cyclic voltammetry. All adducts exert very high solubility in common organic solvents like chloroform, tetrahydrofuran, and toluene.