A series of novel 4- O-alkyltriazolylphenolic derivatives is first synthesized with good to excellent yields via the click reaction of 3-methoxy-4- O-propargylbenzaldehyde or 3-allyl-4- O-propargylacetophenone and aromatic azide derivatives. Next, the chalcones are prepared via the Claisen-Schmidt method from 4- O-alkylphenylketone derivatives in the presence of the corresponding (hetero)aromatic aldehydes as electrophiles. The structures of the newly synthesized compounds are confirmed from their infrared, nuclear magnetic resonance spectral data, and by elemental analysis. The main advantages of this procedure are the simplicity of the reaction conditions, easily available starting materials, and simple work-up. The antioxidant activity of several of the products is determined using the DPPH (2,2-diphenyl-1-picryl-hydrazyl-hydrate) radical scavenging assay. 4- O-propargylvanillin (IC50 = 14.54 µg/mL) had moderate antioxidant activity.