Dimethylformamide → HCID 13482750, compound

HRID 1085331Notes

Reaction equation

HRID 1085331 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].[C:12]([O:15][CH2:16][CH3:17])(=[O:14])[CH3:13].[CH3:18]N(C=O)C>>[C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH:13]([CH3:18])[C:12]([O:15][CH2:16][CH3:17])=[O:14])=[CH:7][CH:6]=1)(=[O:4])[CH3:2]

Participants

5

Reactant 4

HCID 6228Dimethylformamide2×HCID 74694'-HydroxyacetophenoneHCID 8857Ethyl AcetateHCID 5462222Potassium

Product 1

HCID 13482750HCID 13482750, compound

Conditions

Temperature
80 °C

Procedure

A solution of the potassium salt of 4-hydroxyacetophenone (17.6 g, 0.1 mol) in DMF (50 mL) is added to a solution of ethyl L-2-[(methylsulfonyl)oxy]propanoate (21.5 g, 0.11 mol) in DMF (40 mL) over 15 minutes at 80° C. and stirred at 80° C. for 2 hours. To the reaction is added ethyl acetate (100 mL) and filtered. The filtrate is concentrated under reduced pressure whereupon the product is analyzed by GLC. The product is dissolved in ethyl acetate (250 mL) and extracted with saturated sodium bicarbonate solution (2×100 mL) and water (2×60 mL). The organic phase is dried and concentrated to give ethyl 2-(4-acetylphenoxy)propanoate (20.2 g).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate is concentrated under reduced pressure whereupon the product
  3. dissolutionThe product is dissolved in ethyl acetate (250 mL)
  4. extractionextracted with saturated sodium bicarbonate solution (2×100 mL) and water (2×60 mL)
  5. customThe organic phase is dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-be3f0513aa654429b8286d244c02236e
Source dataset
uspto-grants-1991_04
Patent number
US05008439

Reaction notes

Loading…