P-Cresol → Ethyl (p-tolyloxy)acetate

HRID 1492517

Reaction equation

HRID 1492517 reaction equation
[CH:1]1[C:6]([OH:7])=[CH:5][CH:4]=[C:3]([CH3:8])[CH:2]=1.Br[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:8][C:3]1[CH:4]=[CH:5][C:6]([O:7][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:1][CH:2]=1

Participants

5

Reactant 3

HCID 2879P-CresolHCID 7748Ethyl bromoacetateHCID 11430Potassium Carbonate

Product 1

HCID 4047281Ethyl (p-tolyloxy)acetateYield 96.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In 70 ml of acetone were suspended 5.00 g of p-cresol, 7.72 g of ethyl bromoacetate and 6.39 g of potassium carbonate, and the resulting mixture was refluxed for 12 hours. After the solvent was distilled off under reduced pressure, water was added to the mixture, followed by extraction with methylene chloride. The organic phase was washed with in aqueous 2N sodium hydroxide solution and then with saturated sodium chloride solution, which was then dried over magnesium sulfate. On evaporation of the solvent under reduced pressure, 8.67 g of ethyl 4-methylphenoxyacetate was produced.

Workup

  1. temperaturethe resulting mixture was refluxed for 12 hours
  2. distillationAfter the solvent was distilled off under reduced pressure, water
  3. additionwas added to the mixture
  4. extractionfollowed by extraction with methylene chloride
  5. washThe organic phase was washed with in aqueous 2N sodium hydroxide solution
  6. dry with materialwith saturated sodium chloride solution, which was then dried over magnesium sulfate
  7. customOn evaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-cdee900a5f4f409ca9c8d2c187058b2f
Source dataset
uspto-grants-1994_12
Patent number
US05374641

Linked notes

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