Sulfuric Acid → Methyl 4-bromo-3-methylbenzoate

HRID 1708065Notes

Reaction equation

HRID 1708065 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>[CH3:17][O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([Br:1])=[C:3]([CH3:11])[CH:4]=1

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 flocculent solid was filtered off and dried in vacuo at 40°-45° to give the title compound as a liquid which recrystallised on cooling (10.25 g) m.p. 39.5°-40.5°.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 18 h
  3. customto the cooled reaction
  4. filtrationa flocculent solid was filtered off
  5. customdried in vacuo at 40°-45°

Sources & evidence

ORD record
ord-bad66fbf79f5454295c2366852c6c561
Source dataset
uspto-grants-1994_10
Patent number
US05356893

Reaction notes

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