Alternative syntheses of Suberosin (V) as well as Osthol (I) have been described. When the metal salts of 2-hydroxy-4-methoxybenzaldehyde (XI), such as Li, Na, K, Ca and Ti salt, were treated with ƒÁƒÁ,y-dimethylallyl bromide in benzene and water, the four compounds, 3-ƒÁ,ƒÁ-dimethylallyl-2-hydroxy-4-methoxybenzaldehyde (IV), 5-ƒÁ,ƒÁ-dimethyl-ally1-2-hydroxy-4-methoxybenzaldehyde (VIII), 2-ƒÁ,ƒÁ-dimethylallyloxy-4-methoxybenzaldehyde (IX) and 2-ƒÁ,ƒÁ-dimethylallyl-5-methoxyphenol (X) were obtained. Furthermore, IX was converted to VIII by the thermal rearrangement of the y,ydimethylallyl group. In 1934 Spdth, et al.3) reported the synthesis of Osthol (I), a naturally occurring-coumarin which posseses the ƒÁ,ƒÁ-dimethylallyl side chain, by the Parkin condensation reaction of 3-ƒÁ ,ƒÁ-dimethylally1-2-hydroxy-4-methoxybenzaldehyde (IV) with acetic anhydride. Recent work on the synthesis of Suberosin (V),4) 7-methoxy-6-ƒÁ,ƒÁ-dimethylallylcoumarin, was reported. The treatment of 5-ƒÁ,ƒÁ-dimethylally-2,4-dihydroxybenzaldehyde (XIV) with sodium acetate and acetic anhydride gave 7-acetoxy-6-ƒÁ,ƒÁ-dimethylallylcoumarin (XIII). Mild alkaline hydrolysis of XIII produced 7-hydroxy-6-ƒÁ,ƒÁ-dimethylallylcoumarin (XII), whose methylation with diazomethane afforded Suberosin (V). The synthesis of the intermediates IV and XIV, however, did not proceed satisfactorily under the reaction conditions described. It was described that the sodium salt of 2-hydroxy