4-Methoxyphenol → Ethyl 2-(4-methoxyphenoxy)acetate

HRID 1777102Notes

Reaction equation

HRID 1777102 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.Br[C:11](C)(C)[C:12]([O:14][CH2:15][CH3:16])=[O:13].C([O-])([O-])=O.[K+].[K+]>CC#N.O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 90154-MethoxyphenolHCID 11430Potassium CarbonateHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl ester

Product 1

HCID 240125Ethyl 2-(4-methoxyphenoxy)acetate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-methoxyphenol (500 mg, 4.03 mmol) in CH3CN (10 mL) was added ethyl 2-bromo-2-methylpropanoate (807 mg, 4.84 mmol) and K2CO3 (3 g, 21.7 mmol) at 25° C. The mixture was refluxed for 16 h. The mixture was then diluted with water (100 mL), extracted with ethyl acetate (2×50 mL) and the combined organic layers washed with brine (30 mL), dried over Na2SO4 and concentrated to give the title compound which was used in next step without further purification.

Workup

  1. temperatureThe mixture was refluxed for 16 h
  2. extractionextracted with ethyl acetate (2×50 mL)
  3. washthe combined organic layers washed with brine (30 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-72851e060c6f41aab8554c24108e142d
Source dataset
uspto-grants-2016_02
Patent number
US09266836B2

Reaction notes

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