The Smythe Reagent: ~1.6 M LiOH in Hexane

Chemistry
Written By Günther Schlonk

Abstract: The Smythe reagent is an approximately 1.6 M suspension of LiOH in hexane, and is ubiquitous in synthetic chemistry laboratories worldwide. While commercially available, it is more frequently prepared from n-butyllithium, usually by accident. We describe a range of applications for this reagent, such as the O-lithiation of carboxylic acids, hydrolysis of ethyl esters and chlorophosphines, racemisation of alpha-stereocenters and poly-Claisen condensations.

Günther Schlonk
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