Reactions of α-Chloro Epoxides. 1. Hydrolysis of 1,3-Dichloropropene Oxide

Article abstract of DOI:10.1021/jo00320a029

A reinvestigation of the hydrolysis of 1,3-dichloropropene oxide (1) is reported.In contrast to a previous report, the hydrolysis product is 2-hydroxy-3-chloropropanal (4), which dimerizes to 2,5-dihydroxy-3,6-bis(chloromethyl)-1,4-dioxane (5).The α-chloroacrylaldehyde (2) originally reported as the hydrolysis product is derived from the primary thermal isomerization product 2,3-dichloropropanal (3).