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Selective hydroxy group protection of gallic acid

An efficient procedure allowing selective differentiation of the 4-hydroxy group of Me gallate was reported. Me gallate was triacetylated to give 3,4,5-tris(acetyloxy)benzoic acid Me ester which was then regioselectively deacetylated to give the 3,5-tris(acetyloxy)-4-alkoxybenzoic acid Me esters I (R = alkyl, allyl, benzyl). [on SciFinder (R)]

    Keywords: Regiochemistry (prepn. of bis(acetyloxy)alkoxybenzoates by regioselective protection/deprotection of Me gallate) ; gallic acid hydroxy group protection; alkoxy bisacetyloxy benzoate prepn regiochem

    Note:

    CAN 125:142205

    25-18

    Benzene, Its Derivatives, and Condensed Benzenoid Compounds

    Institut de Chimie des Substances Naturelles,Gif-sur-Yvette,Fr.

    Journal

    0039-7911

    written in English.

    99-24-1 (Methyl gallate) Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of bis(acetyloxy)alkoxybenzoates by regioselective protection/deprotection of Me gallate); 1147-85-9P; 13089-97-9P; 20189-90-6P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. of bis(acetyloxy)alkoxybenzoates by regioselective protection/deprotection of Me gallate); 884-35-5P (4-Hydroxy-3,5-dimethoxybenzoic acid methyl ester); 21022-88-8P; 24093-81-0P; 102019-30-7P; 180068-85-3P; 180068-86-4P; 180068-87-5P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of bis(acetyloxy)alkoxybenzoates by regioselective protection/deprotection of Me gallate)

    Reference

    Record created on 2010-11-25, modified on 2016-08-08

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