3-Methylbenzoic acid → Benzoic acid, 3-methyl-, methyl ester

HRID 1174500Notes

Reaction equation

HRID 1174500 reaction equation
[C:1]1([CH3:10])[CH:6]=[CH:5][CH:4]=[C:3]([C:7]([OH:9])=[O:8])[CH:2]=1.S(Cl)(Cl)=O.[C:15]([O-])(O)=O.[Na+]>CO>[CH3:15][O:8][C:7]([C:3]1[CH:2]=[C:1]([CH3:10])[CH:6]=[CH:5][CH:4]=1)=[O:9]

Participants

5

Reactant 3

HCID 74183-Methylbenzoic acidHCID 24386Thionyl ChlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 7435Benzoic acid, 3-methyl-, methyl esterYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
5 °C

Procedure

To a solution of m-toluic acid (175 g, 1.28 mol) in methanol (2 L) was added dropwise thionylchloride (612 g, 5.14 mol) under stirring at 5° C. The mixture was refluxed overnight, then the solvent evaporated. The residue obtained was treated with a 10% aqueous NaHCO3 solution (pH ˜8). The product was extracted with ethyl acetate, washed with water and dried. The solvent was removed and the crude was purified by column chromatography (pet ether/ethyl acetate) to give methyl-m-toluate as colorless liquid (180 g, 93%).

Workup

  1. temperatureThe mixture was refluxed overnight
  2. customthe solvent evaporated
  3. customThe residue obtained
  4. extractionThe product was extracted with ethyl acetate
  5. washwashed with water
  6. customdried
  7. customThe solvent was removed
  8. customthe crude was purified by column chromatography (pet ether/ethyl acetate)

Sources & evidence

ORD record
ord-8038bc2f461d492abff4cf19c9ea3cdf
Source dataset
uspto-grants-2010_11
Patent number
US07838522B2

Reaction notes

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