Hydrogen Peroxide → 2,3,4-Trimethoxyphenol

HRID 1527669Notes

Reaction equation

HRID 1527669 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6](C=O)=[C:5]([O:11][CH3:12])[C:4]=1[O:13][CH3:14].[OH:15]S(O)(=O)=O.OO.CCOC(C)=O>CO>[CH3:12][O:11][C:5]1[C:4]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:10]=[CH:9][C:6]=1[OH:15]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 1118Sulfuric AcidHCID 8857Ethyl Acetate2×HCID 750062,3,4-Trimethoxybenzaldehyde

Product 1

HCID 6035772,3,4-TrimethoxyphenolYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Following a modified procedure by Tremblay et al.,17 2,3,4-trimethoxybenzaldehyde (16, 6.075 g, 31.0 mmol) was dissolved in MeOH (60.0 mL), and then H2SO4 (0.6 mL) and 35% aq. H2O2 (4.0 mL, ˜40 mmol) was added at room temperature. The reaction was then heated to reflux for 2 hrs and monitored by TLC (1:4 EtOAc:hexanes) for completion. When the reaction was complete the solution was cooled and extracted with ethyl acetate. The layers are separated and the organic layer was washed with brine, dried over MgSO4, and filtered. Flash chromatography (1:4 EtOAc:hexanes) provides 17 (5.564 g, 30.2 mmol, 98%) as a light red oil.

Workup

  1. temperatureThe reaction was then heated
  2. temperatureto reflux for 2 hrs
  3. temperaturewas cooled
  4. extractionextracted with ethyl acetate
  5. customThe layers are separated
  6. washthe organic layer was washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered

Sources & evidence

ORD record
ord-440cce232441443b8fe6444270feaaf1
Source dataset
uspto-grants-2015_07
Patent number
US09089605B2

Reaction notes

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