Abstract
An efficient and clean preparation of acylals from aromatic aldehydes in the presence of synthetic phosphates (flourapatite and hydroxyapatite doped with ZnCl2 and ZnBr2) and acetic anhydride was achieved easily in high yields (86% - 97%) at room temperature under solvent-free conditions. Deprotection of the resulting acylals has also been attained by using the same catalysts under microwave irradiation. This method consistently has advantage of excellent yields (82% - 96%) and a short reaction time (3 - 4 min).
Highlights
Open AccessThere has been an increasing emphasis among researchers from both academia and industry to design synthetic strategies keeping in view the principles of “Green Chemistry” [1]
The 1,1-diacetates have been introduced as a suitable protection group for aldehyde because of their remarkable stability to neutral and basic conditions [7]. They can be converted into other useful functional groups by reaction with appropriate nucleophiles [8] and used as carbonyl surrogates for asymmetric synthesis [9]. 1,1-Diacetates, on the other hand, are ambident substrates containing two types of reactive carbon centres, the carbon atom of the protected aldehyde function and the carbonyl group in the ester moieties [10]
The catalytic activity of the materials prepared has been evaluated in the protection of aromatic aldehydes
Summary
There has been an increasing emphasis among researchers from both academia and industry to design synthetic strategies keeping in view the principles of “Green Chemistry” [1]. These factors are especially important in industry. The 1,1-diacetates (acylals) have been introduced as a suitable protection group for aldehyde because of their remarkable stability to neutral and basic conditions [7] They can be converted into other useful functional groups by reaction with appropriate nucleophiles [8] and used as carbonyl surrogates for asymmetric synthesis [9]. We wish to report a mild, convenient and green methodology for the synthesis and deprotection of acylals from aromatic aldehydes using ZnCl2/FAP, ZnBr2/FAP, ZnCl2/HAP and ZnBr2/HAP
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