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Synthesis of carboxylic acids by hydrolysis or saponification

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Name Reactions


Favorsky Reaction


Protecting Groups


Benzyl esters


Recent Literature


N,N-diarylammonium pyrosulfate efficiently catalyzes the hydrolysis of esters under organic solvent-free conditions. This reverse micelle-type method is successfully applied to the hydrolysis of various esters without the decomposition of base-sensitive moieties and without any loss of optical purity for α-heterosubstituted carboxylic acids.
Y. Koshikari, A. Sakakura, K. Ishihara, Org. Lett., 2012, 14, 3194-3197.


An interesting example of a selective deprotection of tert-butyl esters is reported.
E. Marcantoni, M. Massaccesi, E. Torregiani, G. Bartoli, M. Bosco, L. Sambri, J. Org. Chem, 2001, 66, 4430-4432.


A highly efficient semi-two-phase reaction using THF-aqueous NaOH at 0C provides half-esters from symmetric diesters in high yields. Diesters that afforded the corresponding half-esters in quantitative yields all possess two carboalkoxy groups in "cis" or "geminal" orientation.
S. Niwayama, J. Org. Chem., 2000, 65, 5834-5836.

Related


Aluminum powder and iodine in anhydrous acetonitrile mediate a one-pot deprotecting of alkyl carboxylates under nonhydrolytic conditions. Cleavage of lactones affords the corresponding ω-iodoalkylcarboxylic acids. This method enables the selective cleavage of alkyl carboxylic esters in the presence of aryl esters.
D. Sang, H. Yue, Y. Fu, J. Tian, J. Org. Chem., 2021, 86, 4254-4261.