Ethanol → HCID 87061641, compound

Participants

Reaction Steps

150.3 g (0.63 mol) of cyclopentadecanolide were dissolved in 500 ml of acetonitrile under a nitrogen atmosphere, and 229.0 g (1.53 mol) of sodium iodide were added. 170 ml (1.34 mol) of trimethylsilyl chloride were added dropwise through a septum. The mixture was heated under reflux for 18 hours. 158.5 g (3.44 mol) of ethanol were cautiously added to the boiling reaction mixture, which was heated under reflux for a further 2 hours and then allowed to cool to room temperature. 500 ml of diethyl ether were added and the mixture was extracted three times with 500 ml of 1N sodium hydroxide solution each time. The aqueous phases were back-extracted with 300 ml of diethyl ether, and the solvent was removed from the combined organic phases in vacuo. The residue was crystallized from methanol twice at −20° C. Drying in vacuo for several days resulted in 202.3 g (0.51 mol, 81%) of ethyl 15-iodopentadecanoate. Although the product was obtained in good purity, it had an intense odor of precursor owing to very small amounts of lactone (perfumed!).

Provenance & Evidence