A new, convenient and sustainable protocol for the aldol condensation of chroman‐4‐one derivatives with aldehydes using iron as a catalyst under microwave irradiation in the presence of green solvent (2‐methyl‐THF) is presented. The protocol offers a very simple, cost efficient and environmentally benign procedure with good to excellent yields of 3‐benzylidene‐4‐chromanone derivatives. The methodology is demonstrated to be useful for the synthesis of homoisoflavanoids Boundecullin, Sappanone A and their derivatives. The present method offers a potential to generate a quick library of homoisoflavanoids and their synthetic derivatives of medicinal importance.