Potassium Carbonate → Methyl 4-((3-benzoylphenoxy)methyl)benzoate

HRID 332674Notes

Reaction equation

HRID 332674 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][CH:15]=1)[C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:6].[C:16](=O)([O-])[O-].[K+].[K+].Br[C:23]1[CH:32]=[CH:31][C:26]([C:27]([O:29][CH3:30])=[O:28])=[CH:25][CH:24]=1>CN(C)C=O.O>[C:5]([C:4]1[CH:3]=[C:2]([CH:15]=[CH:14][CH:13]=1)[O:1][CH2:16][C:23]1[CH:32]=[CH:31][C:26]([C:27]([O:29][CH3:30])=[O:28])=[CH:25][CH:24]=1)(=[O:6])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 12081Methyl 4-bromobenzoateHCID 830503-Hydroxybenzophenone

Product 1

HCID 71093281Methyl 4-((3-benzoylphenoxy)methyl)benzoateYield 99%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a stirred solution of 3-hydroxybenzophenone (1.00 g, 5.04 mmol) in dimethyl formamide (10 mL), was added potassium carbonate (1.05 g, 7.61 mmol), and the mixture was stirred for 10 minutes at room temperature. Methyl 4-bromobenzoate (1.30 g, 6.05 mmol) in dimethyl formamide (5 mL) was added, and the reaction mixture allowed to stir at room temperature for 16 hours. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic extract was washed with brine, dried (MgSO4), and concentrated under reduced pressure. The crude material was purified by silica gel chromatography eluting with 0-17% ethyl acetate in iso-hexane to afford the title compound (1.64 g, 99%).

Workup

  1. stirringto stir at room temperature for 16 hours
  2. extractionextracted with ethyl acetate
  3. extractionThe organic extract
  4. washwas washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe crude material was purified by silica gel chromatography
  8. washeluting with 0-17% ethyl acetate in iso-hexane

Sources & evidence

ORD record
ord-5cd8fdf9312248fd9d88485ade8b4112
Source dataset
uspto-grants-2014_11
Patent number
US08877774B2

Reaction notes

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