4'-Hydroxyacetophenone → Methyl 2-(4-acetylphenoxy)propanoate

HRID 1085329Notes

Reaction equation

HRID 1085329 reaction equation
[K].[CH3:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]([OH:11])=[CH:9][CH:10]=1)=[O:4].Cl[CH:13]([CH3:18])[C:14]([O:16][CH3:17])=[O:15]>CN(C)C=O>[C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH:13]([CH3:18])[C:14]([O:16][CH3:17])=[O:15])=[CH:7][CH:6]=1)(=[O:4])[CH3:2]

Participants

5

Reactant 3

HCID 74694'-HydroxyacetophenoneHCID 28659Methyl 2-chloropropionateHCID 5462222Potassium

Product 1

HCID 14717334Methyl 2-(4-acetylphenoxy)propanoateYield 80.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
87.5 °C

Procedure

To a solution of the potassium salt of 4-hydroxyacetophenone (25.0 g, 0.14 mol) in dimethylformamide (DMF) (100 mL) is added methyl 2-chloropropanoate (24.5 g, 0.20 mol) over 30 minutes and stirred at 85-90° C. for 3 hours under nitrogen. The reaction is filtered to remove KCl and the filtrate is concentrated under reduced pressure to remove DMF and the product analyzed by GLC. The product is dissolved in ethyl acetate (300 mL) and extracted with 2N NaOH (2×100 mL) and water (100 mL). The organic phase is dried and concentrated to give pure methyl 2-(4-acetylphenoxy)propanoate (25 g) (yield 64%).

Workup

  1. filtrationThe reaction is filtered
  2. customto remove KCl
  3. concentrationthe filtrate is concentrated under reduced pressure
  4. customto remove DMF
  5. dissolutionThe product is dissolved in ethyl acetate (300 mL)
  6. extractionextracted with 2N NaOH (2×100 mL) and water (100 mL)
  7. customThe organic phase is dried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-ac68934f827e481a9fb094951a877288
Source dataset
uspto-grants-1991_04
Patent number
US05008439

Reaction notes

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