Acetone → HCID 19758718, compound

HRID 1586636Notes

Reaction equation

HRID 1586636 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].CC([C:20]1[CH:21]=[CH:22][C:23]([OH:26])=[CH:24][CH:25]=1)=O.[C:27](=[O:30])([O-])[O-:28].[K+].[K+].O.[CH3:34]C(C)=O>>[C:27]([O:28][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:22][CH:21]=1)(=[O:30])[CH3:34]

Participants

6

Reactant 5

HCID 180AcetoneHCID 962WaterHCID 74694'-HydroxyacetophenoneHCID 11430Potassium CarbonateHCID 235144Ethyl 11-bromoundecanoate

Product 1

HCID 19758718HCID 19758718, compoundYield 65%

Procedure

A mixture of the bromoester from (a) (55.3 g, 0.19 mol), 4-hydroxyacetophenone (25.7 g, 0.19 mol) and potassium carbonate (26.1 g, 0.19 mol) in acetone (250 ml) was heated to reflux with stirring for 2 days. After cooling to room temperature, water (500 ml) was added and the whole mixture extracted with ethyl acetate (3×300 ml). The combined extracts were then washed with 3N sodium hydroxide solution (300 ml), water (2×300 ml), 3N HCl solution (200 ml) and water (2×300 ml). After drying over MgSO4 the solvent was removed by evaporation under reduced pressure and the residue recrystallized from methanol to give a white solid (42.9 g, 65%).

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. extractionthe whole mixture extracted with ethyl acetate (3×300 ml)
  4. washThe combined extracts were then washed with 3N sodium hydroxide solution (300 ml), water (2×300 ml), 3N HCl solution (200 ml) and water (2×300 ml)
  5. dry with materialAfter drying over MgSO4 the solvent
  6. customwas removed by evaporation under reduced pressure
  7. customthe residue recrystallized from methanol

Sources & evidence

ORD record
ord-da32151e4df241089bd457c1d2c64e26
Source dataset
uspto-grants-1993_06
Patent number
US05215878

Reaction notes

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