Hydrogen Peroxide → 1,2-Benzenediol, 4-methoxy-

HRID 1706694Notes

Reaction equation

HRID 1706694 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:11])[C:6](=[CH:9][CH:10]=1)C=O.[OH-].[Na+].OO.S([O-])([O-])(=O)=[O:17].[Na+].[Na+].S(S([O-])=O)([O-])=O.[Na+].[Na+]>O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:11])[C:6](=[CH:9][CH:10]=1)[OH:17]

Participants

7

Procedure

4-methoxycatechol was prepared by the method described in Organic Synthesis, Collective Volume 3, page 759: 60.8 g of 4-methoxysalicylaldehyde was added to a stirred solution of 16 g of sodium hydroxide in 200 ml of water. Under nitrogen gas, a solution of 60 g of 30% hydrogen peroxide in water dissolved in 200 ml of water was added drop-by-drop to the resulting solution, held at 35°-40° C. Then sodium sulfate (and a small amount of sodium hydrosulfite to decolorize the mixture) was added until the mixture was saturated. The mixture was extracted with methylene chloride. The resulting residue was extracted with ether. The ether extract was dried (Na2SO4, Na2S2O4) and the solvent was evaporated under reduced pressure, to give crude 4-methoxycatechol (10A).

Workup

  1. custom4-methoxycatechol was prepared by the method
  2. customdescribed in Organic Synthesis, Collective Volume 3, page 759
  3. additionwas added drop-by-drop to the resulting solution
  4. customheld at 35°-40° C
  5. additionwas added until the mixture
  6. extractionThe mixture was extracted with methylene chloride
  7. extractionThe resulting residue was extracted with ether
  8. extractionThe ether extract
  9. dry with materialwas dried (Na2SO4, Na2S2O4)
  10. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-a8e1c1a18b27497f8a9d26da803780ae
Source dataset
uspto-grants-1980_06
Patent number
US04208424

Reaction notes

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