4.4 Article

2,2′-Biphenol-Derived Phosphoric Acid Catalyst for the Dehydra- tive Esterification of Carboxylic Acids with Alcohols

Journal

SYNLETT
Volume -, Issue -, Pages -

Publisher

GEORG THIEME VERLAG KG
DOI: 10.1055/s-0042-1752738

Keywords

alcohols; carboxylic acids; DFT calculations; esterification; green chemistry; organocatalysts; phosphoric acid; pK(a)

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This article describes a new type of catalyst that promotes a dehydrative esterification reaction between carboxylic acids and primary or secondary alcohols without the need to remove water. The reaction is conducted in toluene at 100 degrees C using a 2,2'-biphenol-derived phosphoric acid catalyst (2.5-10 mol%). The catalytic system is demonstrated to be useful for synthesizing pharmaceutically useful and acid-sensitive substrates.
A dehydrative esterification from an equimolar mixture of carboxylic acids and primary or secondary alcohols in toluene at 100 degrees C was promoted without the necessity to remove water by using a simple 2,2'-biphenol-derived phosphoric acid catalyst (2.5-10 mol%). This reaction was also successfully conducted at the gram scale. To demonstrate the synthetic utility of this catalytic system, pharmaceutically useful substrates and acid-sensitive substrates were examined using these acid-base cooperative phosphoric acid catalysts, which exhibit relatively weak Bronsted acidity.

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