Hydrogen Peroxide → 4-(Benzyloxy)-2-isopropoxyphenol

HRID 1805923Notes

Reaction equation

HRID 1805923 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12](C=O)=[C:11]([O:17][CH:18]([CH3:20])[CH3:19])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:21]O>OS(O)(=O)=O.CO.O>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([OH:21])=[C:11]([O:17][CH:18]([CH3:20])[CH3:19])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 784Hydrogen PeroxideHCID 106357444-(Benzyloxy)-2-isopropoxybenzaldehyde

Product 1

HCID 673747764-(Benzyloxy)-2-isopropoxyphenol

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

A solution of 4-(benzyloxy)-2-isopropoxybenzaldehyde (2.76 g, 10.21 mmol) and 30 wt % hydrogen peroxide (1.35 mL, 13.07 mmol) in conc. H2SO4 (0.204 mL) and MeOH (20.4 mL) was stirred for 3 h 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 4-(benzyloxy)-2-isopropoxyphenol, as a colorless oil. LCMS calc.=281.1; found=281.0 (M+Na)+.

Workup

  1. extractionextracted with CH2Cl2 (3×30 mL)
  2. dry with materialThe combined extracts were dried (MgSO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f4c532766a4a43a39f98b699eff92fbf
Source dataset
uspto-grants-2013_01
Patent number
US08354454B2

Reaction notes

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