Water → Ethyl 2-(4-methoxyphenoxy)acetate

HRID 2422209Notes

Reaction equation

HRID 2422209 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.[H-].[Na+].Br[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15].O>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 90154-MethoxyphenolHCID 24758Sodium hydride

Product 1

HCID 240125Ethyl 2-(4-methoxyphenoxy)acetateYield 95.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-methoxyphenol (5.0 g, 40 mmol) in N,N-dimethylformamide (50 mL) was added 60% sodium hydride (1.6 g, 40 mmol) under ice-cooling, and the mixture was stirred for 30 min. Ethyl bromoacetate (7.4 g, 44 mmol) was added thereto, and the mixture was stirred at room temperature for 1 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with water and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=7:1) to give the title compound (8.0 g, yield 94%). oil.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 1 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with water
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=7:1)

Sources & evidence

ORD record
ord-929c868ab9914f3fad8f20ca670c187c
Source dataset
uspto-grants-2011_06
Patent number
US07960369B2

Reaction notes

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