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

HRID 24704

Reaction equation

HRID 24704 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9](C=O)=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.[OH:13]S(O)(=O)=O.OO>>[OH:13][C:9]1[CH:8]=[CH:7][C:6]2[O:1][CH2:2][CH2:3][O:4][C:5]=2[CH:10]=1

Participants

4

Reactant 3

HCID 784Hydrogen PeroxideHCID 1118Sulfuric AcidHCID 2481272,3-Dihydro-1,4-benzodioxin-6-carbaldehyde

Product 1

HCID 91152732,3-Dihydro-1,4-benzodioxin-6-ol

Procedure

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+.

Workup

  1. customevaporated
  2. extractionextracted with CH2Cl2
  3. dry with materialThe extract was dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by column chromatography (silica gel; eluent: hexane to hexane/EtOAc 3:1)

Sources & evidence

ORD record
ord-0b2fe497114b490485af30fa6dd42043
Source dataset
uspto-grants-2005_02
Patent number
US06855843B2

Linked notes

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