4-Isopropylphenol → Ethyl-(4-isopropylphenoxy)acetate

HRID 1269500Notes

Reaction equation

HRID 1269500 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]>CN(C)C=O.O>[CH2:22]([O:21][C:19](=[O:20])[CH2:18][O:10][C:7]1[CH:8]=[CH:9][C:4]([CH:1]([CH3:3])[CH3:2])=[CH:5][CH:6]=1)[CH3:23]

Participants

6

Reactant 3

HCID 74654-IsopropylphenolHCID 7748Ethyl bromoacetateHCID 11430Potassium Carbonate

Product 1

HCID 10822915Ethyl-(4-isopropylphenoxy)acetateYield 98%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-isopropylphenol (1.007 g, 7.39 mmol) in 15 mL dimethylformamide was added potassium carbonate (2.04 g, 14.79 mmol) and ethyl bromoacetate (1.23 mL, 11.09 mmol). The reaction was stirred for 48 h at ambient temperature. The mixture was diluted with 500 mL water and extracted with diethyl ether (2×200 mL). The organic extracts were combined, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resultant oil was flash chromatographed with 10% ethyl acetate/hexanes to yield 1.61 g (98%) of ethyl-(4-isopropylphenoxy)acetate as a clear oil.

Workup

  1. extractionextracted with diethyl ether (2×200 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customchromatographed with 10% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-c321b09b7b974e69af92ae57caa46820
Source dataset
uspto-grants-2007_04
Patent number
US07199243B2

Reaction notes

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