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ChemSusChem. 2018 Jul 11;11(13):2202-2210. doi: 10.1002/cssc.201800684. Epub 2018 Jun 11.

A Two-Step Process for the Synthesis of Hydroxytyrosol.

Author information

1
Dipartimento di Chimica Industriale "Toso Montanari", Alma Mater Studiorum-Università di Bologna, Viale del Risorgimento 4, 40136, Bologna, Italy.
2
Consorzio INSTM, Research Unit of Bologna, Via G. Giusti 9, 50121, Firenze, Italy.
3
CFS Europe SpA, Via Depretis 6, 48123, Ravenna, Italy.

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.

KEYWORDS:

2,2-dimethoxy-acetaldehyde; catalysis; hydrogenation; hydroxyalkylation; hydroxytyrosol

PMID:
29761656
DOI:
10.1002/cssc.201800684

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