Studies on Reaction Products of Pentaerythritol Trichloro Acetate with Sodium Hydroxide in Aqueous Solvent.

Abstract

3, 3-Bischloromethyloxetane can be prepared in a good yield when pentaerythritol trichloroacetate is treated with sodium hydroxide in water. Small amounts of some by-products formed in such treatment were analyzed in order to clarify the mode of reactions. Pentaerythritol trichloroacetate, upon contact with sodium hydroxide in water, is first converted to pentaerythritol trichlorohydrin, which subsequently undergoes ring closure to form 3, 3-bischloromethyloxetane (1). During the course of this reaction, 2-chloromethyl-3-chloro-l-propene (2) is also formed through elimination of formaldehyde. 2, 6-Dioxaspiro [3, 3] heptane, 3-methyleneoxetane, 3, 3-bishydroxymethyloxetane and 3-chloromethyl-3-methoxymethyloxetane are identified as products formed from (1) through the 3-chloromethyl-3-hydroxymethyloxetane intermediate. In an analogous manner, (2) gives 2-hydroxymethyl-3-hydroxy-1-propene and 5-methylene-1, 3-dioxane.