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Issue 17, 2018
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Preparation of acetals from aldehydes and alcohols under basic conditions

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Abstract

A new, simple protocol for the synthesis of acetals under basic conditions from non-enolizable aldehydes and alcohols has been reported. Such reactivity is facilitated by a sodium alkoxide along with a corresponding trifluoroacetate ester, utilizing formation of sodium trifluoroacetate as a driving force for acetal formation. The usefulness of this protocol is demonstrated by its orthogonality with various acid-sensitive protecting groups and by good compatibility with functional groups, delivering synthetically useful acetals complementarily to the synthesis under acidic conditions from aldehydes and alcohols.

Graphical abstract: Preparation of acetals from aldehydes and alcohols under basic conditions

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Publication details

The article was received on 03 Jan 2018, accepted on 13 Feb 2018 and first published on 13 Feb 2018


Article type: Paper
DOI: 10.1039/C8OB00017D
Citation: Org. Biomol. Chem., 2018,16, 3114-3120
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    Preparation of acetals from aldehydes and alcohols under basic conditions

    J. Grabowski, J. M. Granda and J. Jurczak, Org. Biomol. Chem., 2018, 16, 3114
    DOI: 10.1039/C8OB00017D

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