Hydrogen Peroxide → 2,3,4-Trimethoxyphenol

HRID 1805901Notes

Reaction equation

HRID 1805901 reaction equation
[CH3:1][O:2][C:3]1[C:10]([O:11][CH3:12])=[C:9]([O:13][CH3:14])[CH:8]=[CH:7][C:4]=1C=O.[OH:15]O>OS(O)(=O)=O.CO.O>[CH3:1][O:2][C:3]1[C:10]([O:11][CH3:12])=[C:9]([O:13][CH3:14])[CH:8]=[CH:7][C:4]=1[OH:15]

Participants

6

Reactant 2

HCID 784Hydrogen PeroxideHCID 750062,3,4-Trimethoxybenzaldehyde

Product 1

HCID 6035772,3,4-Trimethoxyphenol

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

A solution of 2,3,4-trimethoxybenzaldehyde (1.00 g, 5.10 mmol) and 30 wt/v % hydrogen peroxide (0.672 mL, 6.52 mmol) in conc. H2SO4 (0.102 mL) and MeOH (10.19 mL) was stirred overnight at 25° C. under N2. After this time the mixture was diluted with water (20 mL) and extracted with CH2Cl2 (3×30 mL). The combined extracts were dried (MgSO4) and concentrated in vacuo to afford the crude product. This was purified by flash chromatography (Biotage Horizon, 40M, Si, ˜30 mL/min, 100% hexanes for 360 mL, gradient to 50% EtOAc in hexanes over 2088 mL) to afford 2,3,4-trimethoxyphenol, as a colorless oil. Rf=0.93 (50% EtOAc/hexanes). LCMS calc.=185.1; found=185.2 (M+H)+. 1H NMR (600 MHz, CDCl3): δ 6.62 (d, J=9.0 Hz, 1 H); 6.55 (d, J=8.9 Hz, 1 H); 5.49 (s, 1 H); 3.94 (s, 3 H); 3.89 (s, 3 H); 3.80 (s, 3 H).

Workup

  1. extractionextracted with CH2Cl2 (3×30 mL)
  2. dry with materialThe combined extracts were dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customto afford the crude product
  5. customThis was purified by flash chromatography (Biotage Horizon, 40M, Si, ˜30 mL/min, 100% hexanes for 360 mL, gradient to 50% EtOAc in hexanes over 2088 mL)

Sources & evidence

ORD record
ord-1de88910e9604a33bfb58557cd912a6c
Source dataset
uspto-grants-2013_01
Patent number
US08354454B2

Reaction notes

Loading…