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a mild and convenient ‘dry’ hydrolysis of amides to carboxylic.doc

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a mild and convenient ‘dry’ hydrolysis of amides to carboxylic

Sixth International Electronic Conference on Synthetic Organic Chemistry (ECSOC-6), /ecsoc-6, 1-30 September 2002 [E004] Mathews Reaction : ‘Dry’ Hydrolysis of Nitriles and Amides to Carboxylic Acids Farid CHEMAT Laboratoire de Chimie des Substances Naturelles et des Sciences des Aliments Faculté des Sciences et Technologies, Université de la Réunion 15 avenue René Cassin, B.P. 7151, F-97715 Saint Denis messag cedex 9, La Réunion, France D.O.M chemat@univ-reunion.fr ABSTRACT: Mathews reaction is a one-pot preparation of carboxylic acids from their corresponding nitriles or amides by a ‘dry’ hydrolysis with phthalic acid or anhydride in the absence of water and solvent. Excellent isolated yields (up to 99%) were attained within short reaction times (typically, 30 minutes). KEYWORDS: hydrolysis, microwave, nitrile, amid, carboxylic acid. 1. INTRODUCTION The Mathews reaction, a “dry” hydrolysis procedure of nitriles by phthalic acid or amides by phthalic anhydride to give the corresponding carboxylic acid, is roughly one-century-old 1,2 and during this period, there have been very few studies. 3-7 The need of high reaction temperature, expensive co-reagents (tetrachloro and tetrafluoro phthalic acids or anhydrides) and long reaction periods (6 to 7 days to obtain often only low to moderate yields) have overshadowed its main advantages say simplicity, high yields and selectivity, use of inexpensive reagents, and also some potential applications in organic chemistry. Hydrolysis is a fundamental process in organic chemistry. The introduction of new reagents and the modification of existing ones are a continuous challenge. Reagents are now available for almost every conceivable type of hydrolysis, but in very many instances there are disadvantages associated with their use: high cost, drastic conditions, lack of sensitivity, toxicity, instability, etc. 8-10 We have found that using a moderate pressure of 4 to 10 atm. in a closed reactor under solvent and water-free condit