Organic Chemistry Portal
Reactions > Organic Synthesis Search

Categories: C=O Bond Formation > Synthesis of ketones >

Synthesis of ketones by hydrolysis or deprotection

Name Reactions


Nef Reaction


Nef Reaction


Protecting Groups


Cyclic Acetals


1,3-Dithianes, 1,3-Dithiolanes


Recent Literature


Oximes of various aldehydes and ketones can be converted to the corresponding carbonyl compounds at room temperature in excellent yields with 2-iodylbenzoic acid in water in the presence of β-cyclodextrin.
N. S. Krishnaveni, K. Surendra, Y. V. D. Nageswar, K. R. Rao, Synthesis, 2003, 1968-1969.


N-bromosaccharin is an efficient reagent for the oxidative cleavage of oximes to the corresponding aldehydes and ketones under microwave irradiation in a domestic microwave oven. This procedure features short reaction times, high chemoselectivity (no over-oxidation), easy work-up and high yields.
A. Khazaei, A. A. Manesh, Synthesis, 2004, 1739-1740.


An efficient and convenient procedure has been developed for the hydrolysis of thioacetals/thioketals to the corresponding carbonyl compounds in excellent yields with o-iodoxybenzoic acid (IBX) in presence of β-cyclodextrin (β-CD) in water under neutral conditions at room temperature.
N. S. Krishnaveni, K. Surendra, Y. V. D. Nageswar, K. R. Rao, Synthesis, 2003, 2295-2297.


Perchloric acid adsorbed on silica gel is an extremely efficient, inexpensive, and reusable catalyst for the protection of aldehydes and ketones and the subsequent deprotection. Acetalization was mostly carried out under solvent-free conditions with trialkyl orthoformates, but weakly electrophilic carbonyl compounds and substrates that can coordinate with the catalyst, required the corresponding alcohol as solvent.
R. Kumar, D. Kumar, A. K. Chakraborti, Synthesis, 2007, 299-303.


Er(OTf)3 is a very gentle Lewis acid catalyst in the chemoselective cleavage of alkyl and cyclic acetals and ketals at room temperature in wet nitromethane.
R. Dalpozzo, A. De Nino, L. Maiuolo, M. Nardi, A. Procopio, A. Tagarelli, Synthesis, 2004, 496-498.


I2 catalyzes the deprotection of oximes and imines to the corresponding carbonyl compounds under neutral conditions in a water/surfactant system at 25-40°C in high yields.
P. Gogoi, P. Hazarika, D. Konwar, J. Org. Chem., 2005, 70, 1934-1936.


Silylated cyanohydrins of iodo-substituted aryl, heteroaryl, or cycloalkenyl ketones undergo an I/Mg-exchange using i-PrMgCl·LiCl. After subsequent reactions with electrophiles, a facile deprotection produces polyfunctional ketones in good overall yiels. An extension to aromatic iodoaldehydes is described.
C.-Y. Liu, H. Ren, P. Knochel, Org. Lett., 2006, 8, 617-629.


A number of new reactions of IBX with heteroatom-containing substrates were discovered and their utility was demonstrated. IBX was used for the generation of imines from secondary amines in notably high yields, for the oxidative aromatization of nitrogen heterocycles and for the cleavage of dithianes.
K. C. Nicolaou, C. J. N. Mathison, T. Montagnon, Angew. Chem. Int. Ed., 2003, 42, 4077-4082.