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4-Schiff base-7-benzyloxy-coumarins 5a₁–5h₂ and its derivative 6 were designed and synthesized based on the 7-benzyloxy-coumarin structure as novel antioxidants. The in vitro antioxidant activities screening revealed that 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activities of compounds 5b₁, 5d₁, 5f₁, 5f₂, 5g₁ and 5g₂, and 2,2′-azinobis-(3-ethylbenzthiazoline-6-sulfonate) cation (ABTS⁺) radical scavenging activities of compounds 5a₁, 5b₁, 5c₁, 5c₂, 5d₁, 5e₁, 5e₂, 5f₂, 5g₁, 5g₂ and 5h₁ were better than that of the commercial antioxidant butylated hydroxytoluene (BHT), while the superoxide anion radical scavenging activities of 5a₂ and 5g₂ were stronger than that of the commercial antioxidant butylated hydroxyanisole (BHA), and the hydroxyl radical scavenging activity of 5e₁ was much better than that of the common antioxidant ascorbic acid.