Ethyl bromoacetate → ethyl 2-(2-acetylphenoxy)acetate

HRID 1730831Notes

Reaction equation

HRID 1730831 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:10])[CH3:9].Br[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[O:1][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])(=[O:10])[CH3:9]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 83752'-HydroxyacetophenoneHCID 11430Potassium Carbonate

Product 1

HCID 734889ethyl 2-(2-acetylphenoxy)acetateYield 67.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 136 g of o-hydroxyacetophenone, 167 g of ethyl bromoacetate and 205 g of potassium carbonate was refluxed in 3 l of acetone for 6 hours under heating with stirring. The insoluble materials were filtered from the reaction mixture and the acetone was evaporated from the filtrate. Further, the mixture was distilled to obtain a fraction having a boiling point of 132° C/2 mmHg which was then recrystallized from ligroin to obtain 150 g of the product.

Workup

  1. temperatureunder heating
  2. filtrationThe insoluble materials were filtered from the reaction mixture
  3. customthe acetone was evaporated from the filtrate
  4. distillationFurther, the mixture was distilled
  5. customto obtain a fraction
  6. customwas then recrystallized from ligroin

Sources & evidence

ORD record
ord-20ae4c3c8ba1447f96d307b37e1d0cd2
Source dataset
uspto-grants-1976_11
Patent number
US03994731

Reaction notes

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