Reaction between caproaldehyde 2 and 2-hydroxy-1,4-naphthoquinone 1 under b
oth acidic and basic conditions resulted in the formation of useful compoun
ds including the desired 2-hydroxy-3(1'-hexenyl)-1,4-naphthoquinone 3. The
varied results on the reaction conditions and factors affecting the reactio
n are discussed.