Chemoselective Synthesis of 1,1-Diacetate from Aldehydes Catalyzed by Sulfonated Carbon Nanocage

doi:10.7503/cjcu20130303

Abstract

Abstract:

Acetals are one of the most useful carbonyl protecting groups because of their stability under both neutral and basic media. In addition, acetals can be converted to a variety of other functional groups. Thus, to find a green synthesis method of acetals, the sulfonated carbon nanocage(S-CKT) as a reusable solid acid catalyst was applied to the reaction of aldehydes with acetic anhydride. As a result, a mild and efficient method was developed for the chemoselective preparation of 1,1-diacetates(acylals) from the mixture of aldehydes(2 mmol) and acetic anhydride(5 mmol) catalyzed by S-CKT(30 mg) under room temperature and solvent-free conditions. The reaction takes a shorter time(5—12 min) and gives good to excellent yield(89%—98%). While it is found that ketone doesn't react with acetic anhydride to yield corresponding product under the same conditions. The catalyst was recycled seven times without a distinct loss of activity by simple filtration and washing.

Key words: 1,1-Diacetate, Aldehyde protection, Heterogeneous catalyst, Sulfonated carbon nanocage

CLC Number:

O623
O643.32

TrendMD:

ZHENG Yan-Jun, LI Jiang, LU Jun-Jin, JIA Yu-Cai, LI Bao-Lin. Chemoselective Synthesis of 1,1-Diacetate from Aldehydes Catalyzed by Sulfonated Carbon Nanocage[J]. Chem. J. Chinese Universities, 2013, 34(12): 2738.

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