Facile and sustainable synthesis of the natural antioxidant hydroxytyrosol

Hydroxytyrosol [1, 2-(3,4-dihydroxyphenyl)ethanol], an olive-derived potent natural antioxidant was conveniently prepared from the clove-derived and commercially available eugenol (8, 4-allyl-2-methoxyphenol) using inexpensive reagents in a two-pot four-step process, which successively encompasses a reductive ozonolysis into homovanillyl alcohol (4, 4-hydroxy-3-methoxyphenethanol) and a sodium periodate-mediated oxidative demethylation using a reductive workup.