Methanol → Methyl 4-bromo-2-methylbenzoate

HRID 894170Notes

Reaction equation

HRID 894170 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH3:17]O>>[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9]([O:11][CH3:17])=[O:10])=[CH:4][CH:3]=1

Participants

4

Reactant 3

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

Product 1

HCID 22031226Methyl 4-bromo-2-methylbenzoate

Procedure

Reflux a mixture of 54.30 gm. (0.252 mole) of 5-bromo-o-toluic acid, 400 ml. of methanol and 5 ml. of concentrated sulfuric acid for 18.5 hours. Remove the methanol under vacuum. Dissolve the residue in benzene, wash with water, aqueous sodium bicarbonate solution, water and dry over anhydrous magnesium sulfate. Remove the solvent under vacuum and distill the residual oil to obtain the title product together with the 3-bromo isomer as a colorless oil (yield 41.6 gm., b.p. 132°-135° C./0.1 mm). Chill the oil in a refrigerator for 1 hour and separate the solids to obtain 12.53 gm. of white solid (m.p. 42°-46° C., mainly the 5-bromo isomer).

Workup

  1. temperatureReflux
  2. additiona mixture of 54.30 gm
  3. customRemove the methanol under vacuum
  4. dissolutionDissolve the residue in benzene
  5. washwash with water, aqueous sodium bicarbonate solution, water
  6. dry with materialdry over anhydrous magnesium sulfate
  7. customRemove the solvent under vacuum
  8. distillationdistill the residual oil

Sources & evidence

ORD record
ord-7dab3e05f5144b9c8edcea9f933fa4d6
Source dataset
uspto-grants-1981_08
Patent number
US04282365

Reaction notes

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