Simple Syntheses of 2-Hydroxymethyl-1,3-propanediol and Related Compounds

Abstract
A significantly improved synthesis of 2-hydroxymethyl-1,3-propanediol involves benzoylation of 2-hydroxymethyl-2-nitro-1,3-propanediol, replacement of the nitro group by hydrogen using tributylstannane, and methanolysis. Other simple procedures yield the corresponding trimethanesulfonate, triiodide, and trichloride. Dehydrohalogenation of the triiodide and the trichloride by DBU provides 3-iodo-2-(iodomethyl)propene and the corresponding dichloride, respectively. All of these useful compounds are now readily available for the first time.