4'-Hydroxyacetophenone → Ethyl 2-(4-acetylphenoxy)acetate

HRID 1244103Notes

Reaction equation

HRID 1244103 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]>CC(C)=O>[CH2:22]([O:21][C:19](=[O:20])[CH2:18][O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1)[CH3:23]

Participants

5

Reactant 3

HCID 74694'-HydroxyacetophenoneHCID 7748Ethyl bromoacetateHCID 11430Potassium Carbonate

Product 1

HCID 182681Ethyl 2-(4-acetylphenoxy)acetate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To an ambient slurry of p-hydroxyacetophenone (20 g, 147 mmol) and K2CO3 (30.4 g, 220 mmol) in acetone (150 mL) was added ethyl bromoacetate (17.2 mL, 154 mmol). The slurry was stirred for 18 h and was quenched by the addition of H2O (150 mL) and Et2O (75 mL). The layers were separated, and the aqueous was extracted with additional Et2O (3×75 mL). The combined organic layers were dried with anhydrous Na2SO4, filtered, and concentrated under reduced pressure to give an oil that was used without further purification. MS (ESI) m/e 223 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ ppm 1.22 (t, J=7.12 Hz, 3H), 2.52 (s, 3H), 4.18 (q, J=7.12 Hz, 2H), 4.90 (s, 2H), 7.04 (m, 2H), 7.92 (m, 2H).

Workup

  1. customwas quenched by the addition of H2O (150 mL) and Et2O (75 mL)
  2. customThe layers were separated
  3. extractionthe aqueous was extracted with additional Et2O (3×75 mL)
  4. dry with materialThe combined organic layers were dried with anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto give an oil that
  8. customwas used without further purification

Sources & evidence

ORD record
ord-ac84856c20ee4a1aa9e98630de383b27
Source dataset
uspto-grants-2006_10
Patent number
US07119205B2

Reaction notes

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