Alkylation of p-tert-butylcalix [5] arene with oligoethylene glycol-ditosylates in the presence of CsF affords the 1, 3-bridged calix [5] crowns 1a–c in 51 to 72% yield. In the case of hexaethylene glycol the isomeric 1, 2-bridged calix [5] crown-7 2c was obtained additionally. The calixcrowns were further modified by alkylation of the remaining hydroxyl groups.