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Synfacts 2009(3): 0348-0348  
DOI: 10.1055/s-0028-1087741
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Cleavage of Benzylidene Acetal with PMA/SiO2

Contributor(s): Yasuhiro Uozumi, Takao Osako
P. S. Kumar, G. D. K. Kumar, S. Baskaran*
Indian Institute of Technology, Madras, India
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Publication History

Publication Date:
19 February 2009 (online)

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Significance

Phosphomolybdic acid supported on silica gel (PMA/SiO2) catalyzed the cleavage of benzylidene acetals at room temperature to give the corresponding diols in 75-97% yield (20 examples, equation 1). PMA/SiO2 was also applied to the deacetalization of N-protected 2-phenyl-1,3-oxazolidines (88-95% yield, 5 examples, equation 2). The catalyst was recovered by simple filtration and reused three times without significant loss of catalytic activity.