Ethyl bromoacetate → (2-Acetyl-4-methoxy-phenoxy)-acetic acid ethyl ester

HRID 226263

Reaction equation

HRID 226263 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:5]=1[OH:12])=[O:3].C(=O)([O-])[O-].[K+].[K+].Br[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22]>CCC(C)=O>[CH2:24]([O:23][C:21](=[O:22])[CH2:20][O:12][C:5]1[CH:6]=[CH:7][C:8]([O:10][CH3:11])=[CH:9][C:4]=1[C:2](=[O:3])[CH3:1])[CH3:25]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 697141-(2-Hydroxy-5-methoxyphenyl)ethan-1-one

Product 1

HCID 15643798(2-Acetyl-4-methoxy-phenoxy)-acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 16.6 g (100.0 mmol) of 2-hydroxi-5-methoxyacetophenone, 20 g (208 mmol) of potassium carbonate, 16.7 g (100.0 mmol) of ethyl bromoacetate and 200 ml of MEK is stirred at reflux temperature for 10 hr. The solids are filtered and the filtrate concentrated. The residue is suspended in water and the solid is filtered and dried. Yield: 10.2 g (40%).

Workup

  1. temperatureat reflux temperature for 10 hr
  2. filtrationThe solids are filtered
  3. concentrationthe filtrate concentrated
  4. filtrationthe solid is filtered
  5. customdried

Sources & evidence

ORD record
ord-60bd36e5ee7d4e22abc36d0cbb75c24c
Source dataset
uspto-grants-2009_07
Patent number
US07557212B2

Linked notes

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