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The methylation of some phenols and alcohols with sodium hydride / methyl iodide in tetrahydrofuran at room temperature

✍ Scribed by Barbara A. Stoochnoff; N.Leo Benoiton

Publisher: Elsevier Science
Year: 1973
Tongue: French
Weight: 160 KB
Volume: 14
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)95566-2

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✦ Synopsis

Alcohols and weakly acidic phenols which do not react with diazomethane can be methylated in the presence of acid catalysts 2.3 , but certain hindered alcohols 2,3 and phenols 3 react with difficulty or not at all. We describe here the use of sodium hydride / methyl iodide in tetrahydrofuran (THF) at room temperature for the methylation of alcohols and phenols, and include several compounds not readily methylated by other procedures. 4

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The ground and excited state proton transfer reactions of 4-methyl-2,6-dicarbomethoxyphenol (CMOH) have been studied in water and some alcoholic solvents both in the presence and in the absence of base by means of absorption, emission, and nanosecond spectroscopy at room temperature and 77 K. Solute