Ethyl bromoacetate → (2-Isopropyl-4-methoxy-5-methyl-phenoxy)-acetic acid ethyl ester

HRID 1677263Notes

Reaction equation

HRID 1677263 reaction equation
[CH:1]([C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([CH3:12])=[CH:6][C:5]=1[OH:13])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23]>CC(C)=O>[CH2:25]([O:24][C:22](=[O:23])[CH2:21][O:13][C:5]1[CH:6]=[C:7]([CH3:12])[C:8]([O:10][CH3:11])=[CH:9][C:4]=1[CH:1]([CH3:3])[CH3:2])[CH3:26]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 2515102-Isopropyl-4-methoxy-5-methyl-phenol

Product 1

HCID 59598614(2-Isopropyl-4-methoxy-5-methyl-phenoxy)-acetic acid ethyl esterYield 82.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 2-isopropyl-4-methoxy-5-methyl-phenol (3.933 g, 21.8 mmol) in acetone (100 ml) was added potassium carbonate (20 g, 145 mmol) and ethyl bromoacetate (5 ml, 45.1 mmol). The mixture refluxed over night and was filtered through celite. The filtrate was concentrated under reduced pressure and the residue was partitioned between ethyl acetate and water. The organic phase was washed with brine and dried over anhydrous sodium sulfate. After removal of drying agent, the organic solution was concentrated under reduced pressure. The residue was purified with silica gel chromatography (10% to 15% methylene chloride in hexane) to yield (2-isopropyl-4-methoxy-5-methyl-phenoxy)-acetic acid ethyl ester as white solid (4.78 g, 82%).

Workup

  1. temperatureThe mixture refluxed over night
  2. filtrationwas filtered through celite
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe residue was partitioned between ethyl acetate and water
  5. washThe organic phase was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customAfter removal
  8. customof drying agent
  9. concentrationthe organic solution was concentrated under reduced pressure
  10. customThe residue was purified with silica gel chromatography (10% to 15% methylene chloride in hexane)

Sources & evidence

ORD record
ord-59656624ccb944bcba2e513c0e941883
Source dataset
uspto-grants-2011_08
Patent number
US08008313B2

Reaction notes

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