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Synfacts 2006(11): 1187-1187  
DOI: 10.1055/s-2006-949403
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Solid Silica Sulfuric Acid (SSA)-Catalyzed Acetylation of Aldehydes and Sugars

Contributor(s): Yasuhiro Uozumi, Maki Minakawa
H. Wu*, Y. Shen, L-y. Fan, Y. Wan, D-q. Shi
Xuzhou Normal University, Medical Plant of Jiangsu Province, Xuzhou and Tongji University, Shanghai, P. R. of China
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Publication History

Publication Date:
24 October 2006 (online)

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Significance

Acetylation reactions of aldehydes and sugars using solid silica sulfuric acid (SSA) were described. The SSA-catalyzed (0.06 mol% of SSA) acetylation of aldehydes 1 with acetic anhydride (3-20 equiv) was conducted at room temperature to give the acetylation products 2 in 80-99% yield within 50-70 s. In a similar manner, treatment of sugars 3 with acetic anhydride (4.1-9.0 equiv) in the presence of 0.03-0.06 mol% of SSA for 8-30 min led to the acetylation products 4 in 88-98% yield. In this reaction, the catalyst was recycled at least five times without significant deactivation.