Abstract The title dienone 1, useful for modification, improvement or increasing organoleptic properties of tobacco, sucrose syrups, flavored beverages, was prepared in 40–558 overall yield from isophorone, by chlorination of 2-hydroxy-isophorone (2), rearrangement into 6- chloro-2-hydroxyisophorone (5) and de-hydrochlorination. An excellent yield of 3-chloro-2- hydroxy-4, 4, 6-trimethyl-2, 5-cyclohexenone (12) was obtained by chlorination of 5 ...