Hydrochloric Acid → Methyl 5-Methoxy-2-methylbenzoate

HRID 232868Notes

Reaction equation

HRID 232868 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:9]([O:11][CH3:12])=[O:10])[C:5]([CH3:8])=[CH:6][CH:7]=1.Cl.CN(C)[CH:16]=[O:17]>[Cu](I)I>[CH3:16][O:17][C:2]1[CH:3]=[C:4]([C:9]([O:11][CH3:12])=[O:10])[C:5]([CH3:8])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 316201Methyl 5-bromo-2-methylbenzoate

Product 1

HCID 11745224Methyl 5-Methoxy-2-methylbenzoate

Reagents, catalysts & solvents 1

HCID 83717Copper iodideCatalyst

Procedure

12.6 g of a 28% sodium methylate methanol solution and 4.2 g of copper iodide were added to 5 g of methyl 4-bromo-toluate dissolved in 20 ml of dimethylformamide and the mixture was refluxed under heating for 2 hours. The reaction mixture was adjusted to about pH 2 by adding 1N-hydrochloric acid thereto and extracted with ethyl acetate. and the organic layer was washed with a saturated saline solution and then dried over anhydrous sodium sulfate. The residue obtained by removing the solvent was applied to silica gel column chromatography to obtain 2.47 g of the title compound.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 2 hours
  3. extractionextracted with ethyl acetate
  4. washand the organic layer was washed with a saturated saline solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe residue obtained
  7. customby removing the solvent

Sources & evidence

ORD record
ord-beabbc0321ac4c0eb03c5d181ea16308
Source dataset
uspto-grants-1997_01
Patent number
US05591752

Reaction notes

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