New eco-friendly conditions for Finkelstein reaction employing homogeneous media or aluminasupported reagents, both solventless, were utilized in the bromohydrins and iodohydrins synthesis from 1,3-dichlorohydrin (1,3-DCH), obtained from glycerol. Thus, the trans-halogenation of glycerol-1,3-dichlorohydrin (1) in homogeneous media, using NaI, NaBr salts and organic additives (TBAI, TBAB), led to the synthesis of four different glycerol halohydrins (2a, 2b, 3a, 3b) in regular to excellent conversions (43-96%) and good selectivities to 3a and 2b. Already, the alumina-supported reagents such as KI, KBr, NaBr were used for glycerol-1,3-dichlorohydrin transhalogenation, in the absence of solvent, producing halohydrin mixtures in high conversions (77-99%) and very good selectivity (82%) to 1,3-diiodo-2-propanol (2b).
New efficient and reproductive routes to production of 1,3-dihydroxyacetone (1), 1,3-dichloroacetone (6), 1,3-dibromoacetone (7) and 1,3-diiodoacetone (8) from glycerol 1,3-dichlorohydrin (3) were developed. The synthesis of 1 was processed in three steps from glycerol 2 (1,3-selective chlorination of 2 to 3, oxidation of 3 to 6 and subsequent di-hydroxylation) in 51% overall yield. On the other hand, 7 and 8 were produced from 3, via a trans-bromination and trans-iodination, respectively, followed by oxidation and hydroxylation steps, in 38-52% overall yield. It was used homogeneous media with different reagents (HCl/AcOH, pyridinium chlorochromate (PCC), PCC-HIO 4 ) and heterogeneous media with reagents supported on polymer resins such as Amberlyst ® A26-HCrO 4form, PV-PCC (polyvinyl-pyridinium chlorochromate) and Amberlyst ® A26-OHform or reagents supported on alumina such as KI/Al 2 O 3 , KBr/Al 2 O 3 , in solvent free conditions.
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