Categories: C-O Bond Formation > Synthesis of carboxylic acids >
Synthesis of carboxylic acids by hydrolysis or saponification
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Name Reactions
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 0°C
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.