Hydrogen Peroxide → 2,3-Dihydro-1,4-benzodioxin-6-ol

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Reaction Steps

1,4-Benzodioxan-6-carboxaldehyde (5.20 g) was dissolved in MeCH (60 mL) containing conc. H2SO4 (0.6 mL). At 0° C. an aqueous solution of 30% H2O2 (4.7 mL) was added to the mixture over 5 minutes. The mixture was warmed to room temperature, stirred an additional 18 h and evaporated. The residue was taken up with H2O and extracted with CH2Cl2. The extract was dried (Na2SO4), filtered and evaporated. The residue was purified by column chromatography (silica gel; eluent: hexane to hexane/EtOAc 3:1) to give 6-hydroxy-1,4-benzodioxan (3.85 g). ESMS: m/z 153 MH+.

Provenance & Evidence