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

HRID 1639409Notes

Reaction equation

HRID 1639409 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

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 as 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-7e6d72947cf44c3faa34832f94770324
Source dataset
uspto-grants-1989_11
Patent number
US04883901

Reaction notes

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