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A Two‐Step Process for the Synthesis of Hydroxytyrosol
Author(s) -
Ziosi Paolo,
Paolucci Claudio,
Santarelli Francesco,
Tabanelli Tommaso,
Passeri Sauro,
Cavani Fabrizio,
Righi Paolo
Publication year - 2018
Publication title -
chemsuschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.412
H-Index - 157
eISSN - 1864-564X
pISSN - 1864-5631
DOI - 10.1002/cssc.201800684
Subject(s) - hydroxytyrosol , chemistry , catechol , selectivity , organic chemistry , catalysis , mandelic acid , combinatorial chemistry , antioxidant , polyphenol
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.