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Synthesis 2005(15): 2615-2618  
DOI: 10.1055/s-2005-872175
SPECIALTOPIC
© Georg Thieme Verlag Stuttgart · New York

One-Pot Catalytic Synthesis of 2-(1,2-Dihydroxypropyl)phenol Derivatives from 2-Allylphenols in Aqueous Media

Carole Chevrin, Jean Le Bras*, Françoise Hénin, Jacques Muzart
Unité Mixte de Recherche ‘Réactions Sélectives et Applications’, CNRS-Université de Reims, Champagne-Ardenne, BP 1039, 51687 Reims cedex 2, France
Fax: +33(326)913166; e-Mail: jean.lebras@univ-reims.fr;
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Publication History

Received 14 June 2005
Publication Date:
16 August 2005 (online)

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Abstract

Catalytic amounts of the hydrophilic ligand [(HOCH2CH2NHCOCH2)2NCH2]2 and palladium(II) salts, in the presence of hydrogen peroxide, water and alcohol, allow the direct transformation of 2-allylphenols into 2-(1,2-dihydroxypropyl)phenol derivatives. The mechanism involves sequential isomerisation, epoxidation, and oxirane-opening.

Keywords

alcohols - oxidations - phenols - palladium - epoxidations

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7

Less than 55% yield was obtained from this reaction when carried out in the absence of L H .