Methanol → Methyl 4-bromo-2-methylbenzoate

HRID 403858Notes

Reaction equation

HRID 403858 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([CH3:11])[CH:3]=1.OS(O)(=O)=O.[CH3:17]O>C(OCC)(=O)C>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:17])=[O:7])=[C:4]([CH3:11])[CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 995704-Bromo-2-methylbenzoic acid

Product 1

HCID 22031226Methyl 4-bromo-2-methylbenzoate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-bromo-2-methyl benzoic acid (25 g, 0.116 mol) in methanol (680 mL) was added H2SO4 (12.15 mL) and this reaction mixture was refluxed for about 16 h. The reaction mixture was cooled and the solvent was evaporated to obtain a residue, which was dissolved in ethyl acetate, washed with water and brine, dried over anhydrous sodium sulphate and filtered. The solvent was evaporated to obtain the title compound.

Workup

  1. temperaturethis reaction mixture was refluxed for about 16 h
  2. temperatureThe reaction mixture was cooled
  3. customthe solvent was evaporated
  4. customto obtain a residue, which
  5. washwashed with water and brine
  6. dry with materialdried over anhydrous sodium sulphate
  7. filtrationfiltered
  8. customThe solvent was evaporated

Sources & evidence

ORD record
ord-93e46c612c1042c9ac53e9582eacd7ab
Source dataset
uspto-grants-2014_06
Patent number
US08748426B2

Reaction notes

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