Potassium Carbonate → Methyl 2-(4-isopropyl-3-methylphenoxy)acetate

HRID 1296818Notes

Reaction equation

HRID 1296818 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:5]=1[CH3:11])([CH3:3])[CH3:2].Br[CH2:13][C:14]([O:16][CH3:17])=[O:15].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:13][C:14]([O:16][CH3:17])=[O:15])=[CH:6][C:5]=1[CH3:11])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 185973-Methyl-4-isopropylphenolHCID 60984Methyl bromoacetate

Product 1

HCID 28825594Methyl 2-(4-isopropyl-3-methylphenoxy)acetate

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A solution of 4-isopropyl-3-methylphenol (10.0 g, 67 mmol), methyl bromoacetate (6.6 mL, 70 mmol) and anhydrous potassium carbonate (10.1 g, 73 mmol) in 2-butanone (100 mL) was heated to reflux for 20 h. The mixture was cooled and partitioned between water (350 mL) and ethyl acetate (100 mL). The organic phase was washed with brine, and the aqueous phases were back-extracted in sequence with more ethyl acetate. The extracts were combined, dried over anhydrous magnesium sulfate, filtered and evaporated to afford sufficiently pure product, methyl 2-(4 isopropyl-3-methylphenoxy)acetate, as an oil (15.0 g, 67 mmol, 100%). 1H NMR (CDCl3, 300 MHz): δ 7.05 (1H, d, J=9.3 Hz), 6.64–6.58 (2H, m), 4.51 (2H, s), 3.71 (3H, s), 2.98 (1H, m, J=7.0 Hz), 2.22 (3H, s), 1.11 (6H, d, J=7.0 Hz).

Workup

  1. temperatureto reflux for 20 h
  2. temperatureThe mixture was cooled
  3. custompartitioned between water (350 mL) and ethyl acetate (100 mL)
  4. washThe organic phase was washed with brine
  5. extractionthe aqueous phases were back-extracted in sequence with more ethyl acetate
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-8dc2afe1c74b457aa9607f45190c6588
Source dataset
uspto-grants-2007_07
Patent number
US07247741B2

Reaction notes

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