Methanol → Methyl 3-Bromo-2-methylbenzoate

HRID 1059261Notes

Reaction equation

HRID 1059261 reaction equation
[Br:1][C:2]1[C:3]([CH3:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].S(=O)(=O)(O)O.[OH-].[Na+].[CH3:19]O>>[Br:1][C:2]1[C:3]([CH3:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([O:7][CH3:19])=[O:6]

Participants

5

Reactant 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 27355903-Bromo-2-methylbenzoic Acid

Product 1

HCID 12929135Methyl 3-Bromo-2-methylbenzoate

Procedure

A solution of 3-bromo-2-methylbenzoic acid (9.95 g) and conc. sulfuric acid (0.2 ml) in methanol (50 ml) was stirred at room temperature for 69 h and heated under reflux for 96 h. The reaction mixture was neutralized with 1N aqueous sodium hydroxide solution and concentrated. The residue was diluted with ethyl acetate, washed 3 times with 1N aqueous sodium hydroxide solution and with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give the title compound (10.2 g) as a colorless oil.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 96 h
  3. concentrationconcentrated
  4. additionThe residue was diluted with ethyl acetate
  5. washwashed 3 times with 1N aqueous sodium hydroxide solution
  6. dry with materialwith saturated brine and dried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-794d3142b58b4c319e5381ad7d7b176a
Source dataset
uspto-grants-2003_02
Patent number
US06518257B1

Reaction notes

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