The Synthesis ϒ-nonanoic lactone: The Fragrance of Coconut Oil.

The Synthesis ϒ-nonanoic lactone: The Fragrance of Coconut Oil.

ϒ-nonanoic lactone is used to mimic the scent of coconut in many perfumes, lotions and sunscreens. Here, ϒ-nonanoic lactone was synthesized in a three step process, with heptanol as the starting material. First, the intermediate heptanal was created by oxidizing heptanol with Dess-Martin periodinane (DMP). Since chromium has toxic and carcinogenic properties, a chromium containing oxidizing reagent was replaced with DMP to make the reaction “more green”. Next a Knoevenagel condensation was done with malonic acid and heptanal to create 3-nonenoic acid. Triethylamine was used in this step to form an unsaturated acid. In the final step, ϒ-nonanoic lactone was obtained by reacting 3-nonenoic acid with Amberlyst-15 in a lactonization reaction.