- Expeditious Syntheses to Pharmochemicals 1,3-Dihydroxyacetone, 1,3-Dichloro-, 1,3-Dibromo- And 1,3-Diiodoacetone from Glycerol 1,3-Dichlorohydrin Using Homogenous and Heterogenous Medium
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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-HIO4) and heterogeneous media with reagents supported on polymer resins such as Amberlyst A26-HCrO4– form, PV-PCC (polyvinyl-pyridinium chlorochromate) and Amberlyst A26-OH– form or reagents supported on alumina such as KI/Al2O3, KBr/Al2O3, in solvent free conditions.
- Pereira, Vera Lúcia P.,da Silva, Fernanda Priscila N. R.,da Silva, Sara R. B.,dos Santos, Priscila F.
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p. 1725 - 1731
(2020/10/09)
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- Facile one-pot transformation of carboxylic acid chlorides into 2-substituted allyl alcohols
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The reaction of carboxylic acid chlorides (1) with chloromethyl-lithium generated in situ (1:2 molar ratio) in the presence of lithium iodide leads, after hydrolysis, to the corresponding homologated 2-substituted allyl alcohols (2).
- Barluenga, Jose,Concellon, Jose M.,Fernandez-Simon, Jose L.,Yus, Miguel
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p. 536 - 537
(2007/10/02)
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