Methyl Ethyl Ketone → 2-(4-Phenoxyphenoxy)ethanol

HRID 1669525Notes

Reaction equation

HRID 1669525 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:21][C:22](=[O:25])CC.BrCCO>O>[O:1]([C:8]1[CH:9]=[CH:10][C:11]([O:14][CH2:21][CH2:22][OH:25])=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6569Methyl Ethyl KetoneHCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 132544-Phenoxyphenol

Product 1

HCID 46767252-(4-Phenoxyphenoxy)ethanolYield 62%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 4-Phenoxyphenol (3 g, 16.1 mmol), Potassium carbonate (11.1 g, 80.6 mmol), and 2-Butanone (37.5 mL) was added 2-Bromoethanol (3.14 mL, 44.3 mmol). The resulting mixture was stirred and refluxed at 90° C. overnight under nitrogen. The mixture was poured into 30 mL water solution and extracted with ethyl acetate (EtOAc) (3×10 mL). The combined organic layers were washed with brine (40 mL) and dried over anhydrous Na2SO4. The organic layer was concentrated in vacuo to obtain the crude mixture, which was purified by of silica gel flash chromatography, using EtOAc/hexane (gradient system), to obtain the product (2.3 g, 62%): 1H NMR (400 MHz, CDCL3).

Workup

  1. extractionextracted with ethyl acetate (EtOAc) (3×10 mL)
  2. washThe combined organic layers were washed with brine (40 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationThe organic layer was concentrated in vacuo
  5. customto obtain the crude mixture, which
  6. customwas purified by of silica gel flash chromatography

Sources & evidence

ORD record
ord-887a94a1c010419a9cd0eab1798d9434
Source dataset
uspto-grants-2011_08
Patent number
US07989480B2

Reaction notes

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