Water → 2-Methoxyethyl phenyl ether

HRID 1008516Notes

Reaction equation

HRID 1008516 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH3:10][O:11][CH2:12][CH2:13]Br.O>CN(C)C=O>[CH3:10][O:11][CH2:12][CH2:13][O:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 996PhenolHCID 24758Sodium hydrideHCID 809722-Bromoethyl methyl ether

Product 1

HCID 963752-Methoxyethyl phenyl ether

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of 4.70 g of phenol and 35 mL of dry N,N-dimethylformamide was added dropwise to a stirred suspension of 1.30 g of sodium hydride (95%, dispersion in mineral oil) in 15 mL of dry N,N-dimethylformamide at 5° C. Stirring was continued for 2 hours at 5° C., followed by dropwise addition of 5.20 mL of 2-bromoethyl methyl ether (technical grade, 90%) at 5° C. The mixture was allowed to come to room temperature and stirring was continued for 72 hours. The mixture was poured into water and extracted with diethyl ether. The combined extracts were washed with water and brine, dried (sodium sulfate) and concentrated to give 5.90 g of (2-methoxy-ethoxy)-benzene as an oil. EI-MS: 159 (M+).

Workup

  1. customto come to room temperature
  2. stirringstirring
  3. waitwas continued for 72 hours
  4. extractionextracted with diethyl ether
  5. washThe combined extracts were washed with water and brine
  6. dry with materialdried (sodium sulfate)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d76f545edc3a413bbf87be8da2d5e252
Source dataset
uspto-grants-2004_09
Patent number
US06797710B2

Reaction notes

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