Ligia S. da Silveira Pinto, E. da Silva, M. D. de Souza
May 3, 2016
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Journal
Organic Preparations and Procedures International
Abstract
In recent years, environment-friendly and cost effective chemical processes have been and continue to be developed both academically and industrially. In this context, the development of simple and efficient synthetic methods that reduce the use of reagents and preferably employ no solvent has attracted much interest. 3-Chloro-1,2-propanediol is an important building block in organic synthesis, and one of its stereoisomers has been used in the synthesis of linezolid, a 1,3-oxazolidinone used against antibiotic-resistant gram-positive bacteria. This paper reports an ecofriendly, scalable and highly efficient method for the conversion epichlorohydrin to 3chloro-1,2-propanediol. This procedure involving the addition of water only avoids the use of solvents and acidic or basic conditions to afford 3-chloro-1,2-propanediol in nearly quantitative yield (99%) without the need of purification; no waste is generated. An efficient large scale and optimized preparation is also described (Scheme 1).