Benzylation of hydroxy groups with tertiary amine as a base

The benzylation of hydroxy groups in the presence of tertiary amines is described. A mixture of an alcohol and a benzyl halide afforded the corresponding benzyl ether in good to excellent yields in the presence of diisopropylethylamine. The importance of solventless conditions was observed. The reac...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron 2012-01, Vol.68 (1), p.370-375
Main Authors: Gathirwa, Jeremiah W., Maki, Toshihide
Format: Article
Language:English
Subjects:
Amines
Benzoates
Benzylation
Catalysis
Catalysts
Catalysts: preparations and properties
Chemistry
C–O coupling
Ethers
Exact sciences and technology
Functional groups
General and physical chemistry
Halides
Noncondensed benzenic compounds
Organic chemistry
Preparations and properties
Solventless reaction
Tetrahedrons
Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
Tolerances
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The benzylation of hydroxy groups in the presence of tertiary amines is described. A mixture of an alcohol and a benzyl halide afforded the corresponding benzyl ether in good to excellent yields in the presence of diisopropylethylamine. The importance of solventless conditions was observed. The reaction showed high tolerance to many functional groups including benzoate, even at a reaction temperature of 150°C. Sodium iodide was found to be an efficient catalyst to accelerate the reaction. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2011.10.016