Synthesis of Alkali Metal Carboxylates and Carboxylic Acids Using “Wet” and “Anhydrous” Alkali Metal Hydroxides

Alkali metal carboxylates and carboxylic acids were synthesized using wet and anhydrous alkali metal hydroxides. Lithium, sodium, potassium, and cesium hydroxides, in hydroxylic solvents, have been used indistinctively to perform various reactions. An aqueous solution of tetrabutylammonium hydroxide (TBAH) in methanol, t-butanol, and THF allows the efficient hydrolysis of various esters and N,N-disubstituted amides. The method proved to be efficient every time the resulting acid is soluble in diethyl ether because it facilitates the separation of the ammonium salt, which is insoluble in this solvent. The reactions carried out with naked hydroxide ion whether produced by alkaline fusion, anhydrous ammonium hydroxide, potassium hydroxide generated from potassium hydride and a stoichiometric amount of water, or potassium t-butoxide and water in the ratio of 3/1 (APH) in non hydroxylated solvents behave differently in metal or ammonium hydroxide solutions containing water (WPH).