Diethyl Ether → Methyl 4-methoxy-2-methylbenzoate

HRID 1374831Notes

Reaction equation

HRID 1374831 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH3:12])[CH:3]=1.[CH2:13]([O:15]CC)C>CN(C)C=O.CO>[CH3:9][O:8][C:6](=[O:7])[C:5]1[CH:10]=[CH:11][C:2]([O:15][CH3:13])=[CH:3][C:4]=1[CH3:12]

Participants

5

Reactant 2

HCID 3283Diethyl EtherHCID 22031226Methyl 4-bromo-2-methylbenzoate

Product 1

HCID 13257269Methyl 4-methoxy-2-methylbenzoate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

Methyl 4-bromo-2-methylbenzoate (19.0 mmol) was dissolved in dimethylformamide (2.7 mL) and methanol (1.1 mL), and the solution was heated at 80° C. and then added with CuBr (1.09 mmol). After stirring was continued for 2 hours under heating, the mixture was cooled to room temperature. The mixture was added with diethyl ether (25 mL) and filtered. The filtrate was washed four times with water, an aqueous sodium bicarbonate solution, and then with saturated brine, and dried over sodium sulfated. The drying agent was removed by filtration and the filtrate was concentrated to give the title compound.

Workup

  1. temperatureunder heating
  2. filtrationfiltered
  3. washThe filtrate was washed four times with water
  4. dry with materialan aqueous sodium bicarbonate solution, and then with saturated brine, and dried over sodium
  5. customThe drying agent was removed by filtration
  6. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-d0445513fc9144d0b494848677d2ee5b
Source dataset
uspto-grants-2007_01
Patent number
US07166617B2

Reaction notes

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