Phenol → Acetic acid, 2-phenoxy-, ethyl ester

HRID 18817

Reaction equation

HRID 18817 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17].CCOCC>CN(C=O)C>[CH2:19]([O:18][C:16](=[O:17])[CH2:15][O:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH3:20]

Participants

6

Reactant 4

HCID 996PhenolHCID 3283Diethyl EtherHCID 7748Ethyl bromoacetateHCID 11430Potassium Carbonate

Product 1

HCID 17365Acetic acid, 2-phenoxy-, ethyl esterYield 94.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of phenol (1.88 g, 20.0 mmol) in DMF (40 mL) is added potassium carbonate (3.03 g, 22.0 mmol) and ethyl bromoacetate (2.34 mL, 21.0 mmol), and the mixture is stirred at 70° C. for 18 h. The mixture is cooled to RT, Et2O is added, and the mixture is washed with water, brine, then dried (MgSO4), and filtered. The filtrate is evaporated, and the residue is vacuum distilled to give 3.39 g of the product 430.

Workup

  1. temperatureThe mixture is cooled to RT
  2. washthe mixture is washed with water, brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customThe filtrate is evaporated
  6. distillationdistilled

Sources & evidence

ORD record
ord-02525e846e0e4b539bc293ebb0da1661
Source dataset
uspto-grants-2010_06
Patent number
US07741493B2

Linked notes

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