Iodoethane → 1-(4-ethoxy-2-hydroxyphenyl)ethanone

HRID 859633Notes

Reaction equation

HRID 859633 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7](I)[CH3:8].[OH:10][C:11]1[CH:16]=[C:15]([OH:17])[CH:14]=[CH:13][C:12]=1[C:18](=[O:20])[CH3:19]>CN(C=O)C>[CH2:7]([O:17][C:15]1[CH:14]=[CH:13][C:12]([C:18](=[O:20])[CH3:19])=[C:11]([OH:10])[CH:16]=1)[CH3:8]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 69902',4'-DihydroxyacetophenoneHCID 11430Potassium Carbonate

Product 1

HCID 27751631-(4-ethoxy-2-hydroxyphenyl)ethanoneYield 69.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (13.6 g, 99 mmol) followed by ethyl iodide (2.4 mL, 29.6 mmol) were added to a solution of 2′,4′-dihydroxyacetophenone (5 g, 33 mmol) in DMF (50 mL). The mixture was stirred for 4 hours and then partitioned between H2O and EtOAc. The organic layer was washed with satd NaHCO3, brine, dried over Na2SO4 and concentrated to a clear oil. Purification by column chromatography gave the product as a white solid (3.7 g, 63%). 1H NMR (400 MHz, CDCl3): δ 1.43 (t, J=6.8 Hz, 3 H), 2.55 (s, 3 H), 4.07 (d, J=7.1 Hz, 2 H), 6.40 (s, 1 H), 6.43 (d, J=8.8 Hz, 1 H), 7.62 (d, J=8.8 Hz, 1 H), 12.74 (s, 1 H).

Workup

  1. custompartitioned between H2O and EtOAc
  2. washThe organic layer was washed with satd NaHCO3, brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated to a clear oil
  5. customPurification by column chromatography

Sources & evidence

ORD record
ord-46f1c8cc07b04983b8f9e10d5dc3c2dd
Source dataset
uspto-grants-2006_12
Patent number
US07151105B2

Reaction notes

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