The reaction of crotonic acid with ketones using lithium naphthalenide

Abstract

Lithium naphthalenide reacts with crotonic acid in the presence of diethyl-amine to give the α-anion of lithium crotonate. The reaction of this anion with various ketones gives the corresponding hydroxy acids in good yield. For example, from cyclohexanone and crotonic acid, ω-(1?-hydroxycyolohex-1'-yl)crotonic acid was obtained.