Catechol → 2-(2-methoxyethoxy)phenol

HRID 1532989Notes

Reaction equation

HRID 1532989 reaction equation
[C:1]1([C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4])[OH:2].Br[CH2:10][CH2:11][O:12][CH3:13].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[CH3:13][O:12][CH2:11][CH2:10][O:2][C:1]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[OH:4]

Participants

5

Reactant 3

HCID 289CatecholHCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl ether

Product 1

HCID 112752342-(2-methoxyethoxy)phenol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Catechol (10.0 g, 91 mmol), bromoethylmethylether (12.6 g, 91 mmol), and potassium carbonate (12.6 g, 91 mmol) were mixed in ethanol (100 ml) and refluxed for 15 h. The solvent was evaporated and dichloromethane (200 ml) was added. The inorganics were filtered off and the solvent was removed in vacuum. Chromatography on silica gel with 0.5% methanol in dichloromethane as the eluent gave the title compound. Yield 4.5 g, 29%.

Workup

  1. temperaturerefluxed for 15 h
  2. customThe solvent was evaporated
  3. additiondichloromethane (200 ml) was added
  4. filtrationThe inorganics were filtered off
  5. customthe solvent was removed in vacuum

Sources & evidence

ORD record
ord-98c7a295955b4ec39756183a3eac6515
Source dataset
uspto-grants-2001_03
Patent number
US06207662B1

Reaction notes

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