Hydroquinone → 4-(2-Methoxyethoxy)phenol

HRID 1465543Notes

Reaction equation

HRID 1465543 reaction equation
[H-].[Na+].[C:3]1([CH:10]=[CH:9][C:7]([OH:8])=[CH:6][CH:5]=1)[OH:4].CC1C=CC(S(O[CH2:22][CH2:23][O:24][CH3:25])(=O)=O)=CC=1.O>CN(C=O)C>[CH3:25][O:24][CH2:23][CH2:22][O:4][C:3]1[CH:10]=[CH:9][C:7]([OH:8])=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 785HydroquinoneHCID 962WaterHCID 24758Sodium hydrideHCID 86977Ethanol, 2-methoxy-, 1-(4-methylbenzenesulfonate)

Product 1

HCID 133135614-(2-Methoxyethoxy)phenolYield 32.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
65 °C

Procedure

To a solution of 60% sodium hydride (436 mg, 18.2 mmol) in DMF (2.0 mL) was added hydroquinone (1.0 g, 18.2 mmol) in DMF (10.0 mL) dropwisely. The solution was added with 2-methoxyethyl 4-methylbenzenesulfonate (12-2, 2.10 g, 21.8 mmol) dropwisely. The reaction was stirred at 65° C. for 16 h. The solution was cooled to room temperature, poured into icy H2O, and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous MgSO4(s), and concentrated under reduced pressure to give 4-(2-methoxyethoxy)phenol (12-3, 1.0 g), which was used directly for the next step without further purification.

Workup

  1. temperatureThe solution was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous MgSO4(s)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5ed9a1f3f230450a81b9cafdf91ceb58
Source dataset
uspto-grants-2015_04
Patent number
US08999983B2

Reaction notes

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