The Journal of Organic Chemistry

Mechanism of the reaction between benzylmagnesium chloride and carbonyl compounds. A detailed study with formaldehyde

RA Benkeser, DC Snyder

Index: Benkeser, Robert A.; Snyder, Dudley C. Journal of Organic Chemistry, 1982 , vol. 47, # 7 p. 1243 - 1249

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Citation Number: 25

Abstract

The reaction of benzylmagnesium chloride in THF with monomeric formaldehyde has been studied in detail. A mechanism is presented which accounts for the formation of the products, 2-phenylethanol, o-tolylcarbinol, and 0-(2-hydroxyethyl) benzyl alcohol. A change in technique for Grignard titration and formaldehyde addition results in a much-improved mass balance than achieved previously. The decreased yield of the major product, o- ...