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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 40, 2010 - Issue 21
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Original Articles

Silica Phosphoric Acid: An Efficient and Recyclable Catalyst for the Solvent-Free Synthesis of Acylals and Their Deprotection in MeOH

, , , &
Pages 3240-3250 | Received 26 Jul 2009, Published online: 04 Oct 2010
 

Abstract

Silica phosphoric acid was used as an efficient, mild, and recyclable solid catalyst for the synthesis of acylals from various structurally diverse aldehydes and acetic anhydride under solvent-free conditions. The acylation of aldehydes was highly chemoselective, and no ketone was acylated, which provided a method for the synthesis of acylals from aldehydes in the presence of ketones. Silica phosphoric acid–catalyzed deprotection of acylals to the corresponding aldehydes in MeOH has also been developed with excellent yield. The deprotection of the acylals of aromatic aldehydes took priority over those of aliphatic aldehydes.

ACKNOWLEDGMENTS

The authors thank NNSF of China (No. 20972142), the State Key Laboratory of Bio-organic and Natural Products Chemistry, Chinese Academy of Sciences (CAS), the Natural Science Project of Henan Province (2009A150030, 082300420110), and the Innovation Fund of Zhengzhou University (2008CXSY147) for financial support.

Notes

a The isolated yield.

b All the products were characterized by 1H NMR, IR, and mass spectroscopy.

c 4.0 equivalents of Ac2O.

d Time in hours.

e NR, no reaction.

a The yields refer to the isolated pure products.

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