Catechol → 2-(2-Methoxyethoxy)phenol
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
Product 1
Reagents, catalysts & solvents 1
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
- temperaturerefluxed for 15 h
- customThe solvent was evaporated
- additiondichioromethane (200 ml) was added
- filtrationThe inorganics were filtered off
- customthe solvent was removed in vacuum
Sources & evidence
- ORD record
- ord-c2faea9cd1ff4d568b355650ae78f460
- Source dataset
- uspto-grants-2002_11
- Patent number
- US06479491B1
Reaction notes
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