3-Hydroxyacetophenone → HCID 10956102, compound

HRID 2090545Notes

Reaction equation

HRID 2090545 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8](=[O:10])[CH3:9])[CH:5]=[CH:6][CH:7]=1.F[C:12]1[CH:17]=[CH:16][C:15]([C:18](=[O:20])[CH3:19])=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[C:18]([C:15]1[CH:16]=[CH:17][C:12]([O:1][C:2]2[CH:3]=[C:4]([C:8](=[O:10])[CH3:9])[CH:5]=[CH:6][CH:7]=2)=[CH:13][CH:14]=1)(=[O:20])[CH3:19]

Participants

5

Reactant 3

HCID 84873-HydroxyacetophenoneHCID 98284'-FluoroacetophenoneHCID 11430Potassium Carbonate

Product 1

HCID 10956102HCID 10956102, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 1-(3-hydroxyphenyl)ethanone (8 g, 58.7 mmol), 1-(4-fluorophenyl)ethanone (8.1 g, 58.7 mmol) and anhydrous potassium carbonate (16.2 g, 117.5 mmol) in DMSO (150 mL) was stirred for 16 hours at 140° C. The mixture was partitioned between ethyl acetate and water. The aqueous layer was acidified with 1M HCl until pH=6-7 and extracted with ethyl acetate. The combined organics were washed with brine, dried (MgSO4), filtered, and concentrated under reduced pressure. The crude product was chromatographed on silica gel (ethyl actetate/heptane: 1/1) resulting in 1-(3-(4-acetylphenoxy)phenyl)ethanone (11 g, 74%) as a white solid.

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. extractionextracted with ethyl acetate
  3. washThe combined organics were washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was chromatographed on silica gel (ethyl actetate/heptane: 1/1)
  8. customresulting in 1-(3-(4-acetylphenoxy)phenyl)ethanone (11 g, 74%) as a white solid

Sources & evidence

ORD record
ord-a4812ae0837245a3b0d571bf2a0b20af
Source dataset
uspto-grants-2013_05
Patent number
US08436036B2

Reaction notes

Loading…