Catechol → 2-(2-methoxyethoxy)phenol

HRID 1017246Notes

Reaction equation

HRID 1017246 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 dichioromethane (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. additiondichioromethane (200 ml) was added
  4. filtrationThe inorganics were filtered off
  5. customthe solvent was removed in vacuum

Sources & evidence

ORD record
ord-c2faea9cd1ff4d568b355650ae78f460
Source dataset
uspto-grants-2002_11
Patent number
US06479491B1

Reaction notes

Loading…