A Two‐Step Process for the Synthesis of Hydroxytyrosol. Issue 13 (11th June 2018)

• Record Type: Journal Article
• Authors: Ziosi, Paolo; Paolucci, Claudio; Santarelli, Francesco; Tabanelli, Tommaso; Passeri, Sauro; Cavani, Fabrizio; Righi, Paolo
• Is Part Of: ChemSusChem. Volume 11:Issue 13(2018)
• Page Start: 2202
• Page End: 2210
• Publication Date: 2018-06-11
• Subjects: 2, 2-dimethoxy-acetaldehyde -- catalysis -- hydrogenation -- hydroxyalkylation -- hydroxytyrosol; Green chemistry -- Periodicals; Sustainable engineering -- Periodicals; Chemistry -- Periodicals; Chemical engineering -- Periodicals; 660
• DOI: 10.1002/cssc.201800684
• Languages: English
• ISSNs: 1864-5631

Abstract

Abstract: A new process for the synthesis of hydroxytyrosol (3, 4‐dihydroxyphenylethanol), the most powerful natural antioxidant currently known, by means of a two‐step approach is reported. Catechol is first reacted with 2, 2‐dimethoxyacetaldehyde in basic aqueous medium to produce the corresponding mandelic derivative with >90 % conversion of the limiting reactant and about 70 % selectivity to the desired para ‐hydroxyalkylated compound. Thereafter, the intermediate is hydrogenated to hydroxytyrosol by using a Pd/C catalyst, with total conversion of the mandelic derivative and 68 % selectivity. This two‐step process is the first example of a synthetic pathway for hydroxytyrosol that does not involve the use of halogenated components or reduction methodologies that produce stoichiometric waste. It also avoids the complex procedure currently used for hydroxytyrosol purification when it is extracted from wastewater of olive oil production. Abstract : Out of oil : Hydroxytyrosol (3, 4‐dihydroxyphenylethanol), found in olive oil products, is the most powerful natural antioxidant currently known. A two‐step innovative process for the synthesis of hydroxytyrosol is reported. Both steps are conducted in water and under mild conditions to give a much lower E factor than previous syntheses.