Sulfuric Acid → Methyl 4-bromo-3-methylbenzoate

HRID 1721312Notes

Reaction equation

HRID 1721312 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[CH3:11].S(=O)(=O)(O)O.[C:17]([O-])(O)=O.[Na+]>CO>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:17])=[O:7])=[CH:4][C:3]=1[CH3:11]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 821314-Bromo-3-methylbenzoic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 3294148Methyl 4-bromo-3-methylbenzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Bromo-3-methylbenzoic acid (10 g) was suspended in methanol (50 ml) containing conc. sulphuric acid (2 ml). The mixture was heated to reflux for 18 h. On addition of 8% NaHCO3 (100 ml) to the cooled reaction, a solid was formed which was collected by filtration. Drying in vacuo at 40°-45° gave the title compound as a liquid which recrystallised on cooling (10.25 g) m.p. 39.5°-40.5° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 18 h
  3. customto the cooled reaction
  4. customa solid was formed which
  5. filtrationwas collected by filtration
  6. customDrying in vacuo at 40°-45°

Sources & evidence

ORD record
ord-02ddc7dff8c444d68eb3ebf05637e4da
Source dataset
uspto-grants-1996_04
Patent number
US05510350

Reaction notes

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