Ethyl bromoacetate → Ethyl (2-acetyl-3-hydroxyphenoxy)acetate

HRID 978104Notes

Reaction equation

HRID 978104 reaction equation
[CH3:1][C:2]([C:4]1[C:5]([OH:11])=[CH:6][CH:7]=[CH:8][C:9]=1[OH:10])=[O:3].Br[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:17]([O:16][C:14](=[O:15])[CH2:13][O:11][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]([OH:10])[C:4]=1[C:2](=[O:3])[CH3:1])[CH3:18]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 696872',6'-Dihydroxyacetophenone

Product 1

HCID 4673143Ethyl (2-acetyl-3-hydroxyphenoxy)acetate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2,6-dihydroxyacetophenone (40 g), ethyl bromoacetate (48 g) and potassium carbonate (58 g) in acetone (500 ml) was refluxed for 3 hours. The mixture was cooled and filtered. The solution was evaporated to dryness and the crude solid extracted with boiling hexane. Upon cooling, the title compound was obtained.

Workup

  1. temperaturewas refluxed for 3 hours
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. customThe solution was evaporated to dryness
  5. extractionthe crude solid extracted with boiling hexane
  6. temperatureUpon cooling

Sources & evidence

ORD record
ord-5daafc56e4054350848aa44c9f5eec5d
Source dataset
uspto-grants-1987_05
Patent number
US04663347

Reaction notes

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