4'-Hydroxyacetophenone → HCID 13482750, compound

HRID 2254342Notes

Reaction equation

HRID 2254342 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]([CH3:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15]>CN(C=O)C>[C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH:13]([CH3:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:7][CH:6]=1)(=[O:4])[CH3:2]

Participants

5

Reactant 3

HCID 74694'-HydroxyacetophenoneHCID 10807Ethyl 2-chloropropionateHCID 5462222Potassium

Product 1

HCID 13482750HCID 13482750, compoundYield 90.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the potassium salt of 4-hydroxyacetophenone (25.0 g, 0.14 mol) in DMF (100 mL) is added ethyl 2-chloropropanoate (27.3 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 is 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 ethyl 2-(4-acetylphenoxy)propanoate (30 g) (yield 75%); m.p. 49.6° C.; IR (KBr) 1747.7 (vs), 1669.8 (vs); 1H NMR (CDCl3) delta 1.18 (t, J=7.2 Hz, 3H), 1.58 (d, J=6.8 Hz, 3H), 2.46 (s, 3H), 4.15 (q, J=7.2, 2H), 4.77 (q, J=6.8, 1H), 6.83 and 7.84 (dd, J=9.0 Hz, 4H).

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-fa7f17fb6268457ca19d96cc1aab640a
Source dataset
uspto-grants-1993_08
Patent number
US05235090

Reaction notes

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