E. Popovski, K. Mladenovska, A. Panovska
Dec 24, 2010
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0
Influential Citations
1
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Molbank
Abstract
Abstract: In this note, two procedures for the synthesis of (benzoylamino)methyl 4-[(benzoylamino)methoxy]benzoate ( 3 ) are presented. The first procedure is carried out in dioxane/water using benzoylaminomethyl-4-hydroxybenzoate, while the second one employs a suspension of 4-hydroxybenzoic acid in dioxane. In both procedures, benzamidomethyl triethylammonium chloride is used for the benzamidomethylation reaction. Keywords: benzamidomethyl ester; synthesis Methyl 4-methoxybenzoate (also known as methyl anisate) is a white crystalline powder, soluble in alcohol and ether, but insoluble in water. In the nature, it occurs as a volatile compound in mushroom species and plants [1–5]. These types of esters are used as pharmaceutical intermediates and take part in many organic syntheses [6,7]. For example, a new imaging compound, [(125)I]iodoDPA-713, was synthesized in several steps from methyl 4-methoxybenzoate as a tool for quantification of inflammation in preclinical models [6]. Nowadays, methyl 4-methoxybenzoate has application in the flavor and perfume industry as synthetic flavoring substance due to its sweet herbal anis aroma, impressing lilac or magnolia [8,9]. In this note, the synthesis of a new compound, (benzoylamino)methyl 4-[(benzoylamino)methoxy]-benzoate (