A Simple and Versatile Method for the Synthesis of Acetals from Aldehydes and Ketones Using Bismuth Triflate

A Simple and Versatile Method for the Synthesis of Acetals from Aldehydes and Ketones Using Bismuth Triflate

Acetals are obtained in good yields by treatment of aldehydes and ketones with trialkyl orthoformate and the corresponding alcohol in the presence of 0.1 mol % Bi(OTf)3·4H2O. A simple procedure for the formation of acetals of diaryl ketones has also been developed. The conversion of carbonyl compoun...

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Bibliographic Details
Published in:Journal of organic chemistry Vol. 67; no. 15; pp. 5202 - 5207
Main Authors: Leonard, Nicholas M, Oswald, Matthew C, Freiberg, Derek A, Nattier, Bryce A, Smith, Russell C, Mohan, Ram S
Format: Journal Article
Language:English
Published: Washington, DC American Chemical Society 26-07-2002
Subjects:
Aliphatic compounds
Chemistry
Exact sciences and technology
Organic chemistry
Preparations and properties
Ethylene glycol
Mild operating conditions
Benzaldehyde
Alcohol
Aldehyde
Oxygen heterocycle
Ketone
Dioxolane derivatives
Acetal
Bismuth III
Orthoester
Aromatic compound
Chemical synthesis
Methanol
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Summary:Acetals are obtained in good yields by treatment of aldehydes and ketones with trialkyl orthoformate and the corresponding alcohol in the presence of 0.1 mol % Bi(OTf)3·4H2O. A simple procedure for the formation of acetals of diaryl ketones has also been developed. The conversion of carbonyl compounds to the corresponding 1,3-dioxolane using ethylene glycol is also catalyzed by Bi(OTf)3·4H2O (1 mol %). Two methods, both of which avoid the use of benzene, have been developed.
Bibliography:istex:A8E7388ABA35606284ED05B6BA7D40B0BBE6C99B
ark:/67375/TPS-64K5LN52-3
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/jo0258249