2-Ethylphenol → Ethyl (2-ethylphenoxy)acetate

HRID 1766114Notes

Reaction equation

HRID 1766114 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[OH:9])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:16]([O:18][C:19](=[O:22])[CH2:20]Br)[CH3:17]>CN(C=O)C>[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[O:9][CH2:20][C:19]([O:18][CH2:16][CH3:17])=[O:22])[CH3:2]

Participants

5

Reactant 3

HCID 69972-EthylphenolHCID 7748Ethyl bromoacetateHCID 11430Potassium Carbonate

Product 1

HCID 21986411Ethyl (2-ethylphenoxy)acetateYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 2-ethylphenol (5 ml, 42.4 mmoles, 1 eq) in dry DMF (120 ml, 0.35M) was added potassium carbonate (6.45 g, 46.6 mmoles, 1.1 eq) and ethylbromoacetate (4.7 ml, 42.2 mmoles, 1 eq) and heated to 60° C. overnight. After cooling to room temperature the reaction mixture was partitioned between ethyl ether and 1N NaOH. The phases were separated and the organic portion was washed twice with 1N NaOH, twice with H2O, brine, dried over Na2SO4, filtered and concentrated in vacuo to yield 7.2 g (82%) of product.

Workup

  1. temperatureAfter cooling to room temperature the reaction mixture
  2. customwas partitioned between ethyl ether and 1N NaOH
  3. customThe phases were separated
  4. washthe organic portion was washed twice with 1N NaOH, twice with H2O, brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-02aec32f5557491b9232dd2006882c53
Source dataset
uspto-grants-2007_06
Patent number
US07229998B2

Reaction notes

Loading…