Sulfuric Acid → Methyl 4-bromo-3-methylbenzoate

HRID 1708386Notes

Reaction equation

HRID 1708386 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 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. filtrationa flocculent solid was filtered off
  3. customdried in vacuo at 40°-45°

Sources & evidence

ORD record
ord-ec0c333f0cd847129e465919fdb7569d
Source dataset
uspto-grants-1994_10
Patent number
US05358948

Reaction notes

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