Water → 2-Methoxyethyl phenyl ether

HRID 1279041Notes

Reaction equation

HRID 1279041 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-282c5cc08e114a7aa38c2fb49f51bb16
Source dataset
uspto-grants-2002_09
Patent number
US06444672B1

Reaction notes

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