4'-Methoxyacetophenone → HCID 66650188, compound

HRID 884673Notes

Reaction equation

HRID 884673 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][CH:5]=1)=[O:3].[CH3:12][O:13][C:14]1[C:23]([O:24][CH3:25])=[CH:22][CH:21]=[CH:20][C:15]=1[C:16](OC)=[O:17].[H-].[Na+]>CN(C=O)C>[CH3:12][O:13][C:14]1[C:23]([O:24][CH3:25])=[CH:22][CH:21]=[CH:20][C:15]=1[C:16](=[O:17])[CH2:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][CH:5]=1)=[O:3]

Participants

5

Reactant 3

HCID 74764'-MethoxyacetophenoneHCID 24758Sodium hydrideHCID 75075Methyl 2,3-dimethoxybenzoate

Product 1

HCID 66650188HCID 66650188, compoundYield 74.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-methoxyacetophenone (2.0 g, 13.3 mmol) and methyl 2,3-dimethoxybenzoate (3.135 g, 15.98 mmol) in DMF (100 mL), was added a NaH (1.065 g, 26.63 mmol) and the reaction mixture was stirred for 24 h at rt under N2. The reaction mixture was poured into ice water and products were extracted with EtOAc. The organic layer was separated, washed with water, dried and concentrated to afford 1-(2,3-dimethoxy-phenyl)-3-(4-methoxy-phenyl)-propane-1,3-dione (3.1 g, 74%).

Workup

  1. extractionwere extracted with EtOAc
  2. customThe organic layer was separated
  3. washwashed with water
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e1b8f01338084b6dabdcf91ed12f5c2d
Source dataset
uspto-grants-2012_08
Patent number
US08242130B2

Reaction notes

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