P-Toluic Acid → Methyl 4-methylbenzoate

HRID 2249403Notes

Reaction equation

HRID 2249403 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:10])=[O:9])=[CH:6][CH:7]=1.S(Cl)(Cl)=O.[C:15]([O-])(O)=O.[Na+]>CO>[CH3:15][O:9][C:8]([C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=1)=[O:10]

Participants

5

Reactant 3

HCID 7470P-Toluic AcidHCID 24386Thionyl ChlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 7455Methyl 4-methylbenzoateYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of p-toluic acid (175 g, 1.28 mol) in methanol (2 L) was added dropwise thionylchloride (612 g, 5.14 mol) under stiring 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-p-toluate as colorless liquid (180 g, 93%).

Workup

  1. customunder stiring at 5° C
  2. temperatureThe mixture was refluxed overnight
  3. customthe solvent evaporated
  4. customThe residue obtained
  5. extractionwas extracted with ethyl acetate, washed-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-70bce36fc908453282b48177bd271ce7
Source dataset
uspto-grants-2008_01
Patent number
US07314878B2

Reaction notes

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