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Synthesis 1987; 1987(8): 742-745
DOI: 10.1055/s-1987-28072
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Simple Syntheses of 2-Hydroxymethyl-1,3-propanediol and Related Compounds

Stéphan Latour* , James D. Wuest
  • *Département de Chimie, Université de Montréal, Montréal, Québec H3C 3J7 Canada
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Publication Date:
12 September 2002 (online)

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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.

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