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

HRID 2053608Notes

Reaction equation

HRID 2053608 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-0eb881118c914a3083c16c85f93eade3
Source dataset
uspto-grants-2008_02
Patent number
US07326792B2

Reaction notes

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