Abstract
[3851-95-4] C4H4O5 (MW 132.08) InChI = 1S/C4H4O5/c5-3(6)1-2-4(7)9-8/h1-2,8H,(H,5,6)/b2-1- InChIKey = KFHHPVVJLXPHJL-UPHRSURJSA-N (electrophilic reagent capable of reacting with many functional groups; delivers oxygen to alkenes and amines2) Alternate Names: permaleic acid; PMA. Solubility: sol CH2Cl2, CHCl3 and water. Form Supplied in: not available commercially. Analysis of Reagent Purity: assay using iodometry.3 Preparative Methods: (a) to a cooled (0 °C) and stirred mixture of 90% Hydrogen Peroxide (caution) (11.6 g, 0.34 mol) and CH2Cl2 (150 mL) is added in one batch 39.2 g (0.4 mol) of freshly crushed Maleic Anhydride. When the major portion of the anhydride has reacted, the reaction mixture is heated to reflux.2 (b) 0.1 mol of 88% H2O2, 0.13 mol of maleic anhydride, CHCl3 (19.5 mL), and DMF (0.5 mL) are stirred at 20 °C for 1.5 h to give the reagent, essentially free from H2O2.4 Handling, Storage, and Precautions: reasonably stable in CH2Cl2 solution, decomposing to the extent of 5% in 6 h at rt. Since peroxy acids are potentially explosive, care is required while carrying out the reactions; during workup, test for peroxides before solvent removal. This reagent should be handled in a fume hood.
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