Potassium Carbonate → (2-Acetyl-3-hydroxy-phenoxy)-acetic acid tert-butyl ester

HRID 29478

Reaction equation

HRID 29478 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].C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21]>CC(C)=O>[C:23]([O:22][C:20](=[O:21])[CH2:19][O:11][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]([OH:10])[C:4]=1[C:2](=[O:3])[CH3:1])([CH3:26])([CH3:25])[CH3:24]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 696872',6'-DihydroxyacetophenoneHCID 79177tert-Butyl bromoacetate

Product 1

HCID 68714827(2-Acetyl-3-hydroxy-phenoxy)-acetic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 2,6-dihydroxyacetophenone (35.37 g, 0.23 moles), potassium carbonate (51.4 g, 0.37 moles), and t-butyl bromoacetate (28.4 mL, 0.23 moles) in 440 mL of acetone was heated at reflux for 1.5 hours. It was then cooled to room temperature and filtered. The filter cake was washed with acetone and the combined mother liquors were concentrated in vacuo. (2-Acetyl-3-hydroxy-phenoxy)-acetic acid tert-butyl ester was isolated as thick yellow oil, which was used directly used for the next step.

Workup

  1. temperatureat reflux for 1.5 hours
  2. filtrationfiltered
  3. washThe filter cake was washed with acetone
  4. concentrationthe combined mother liquors were concentrated in vacuo

Sources & evidence

ORD record
ord-110f91f4fca842a19f7388dc5a948ecb
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Linked notes

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