p-Toluenesulfonic acid → (R)-(-)-Methyl mandelate

HRID 478991Notes

Reaction equation

HRID 478991 reaction equation
[C:1]([OH:11])(=[O:10])[C@@H:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[OH:3].[C:12]1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[CH3:12][O:10][C:1](=[O:11])[C@@H:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[OH:3]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 11914(-)-Mandelic acid

Product 1

HCID 2724623(R)-(-)-Methyl mandelate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Into methanol (20 ml) were added (R)-mandelic acid (5.0 g) and p-toluenesulfonic acid (0.1 g), and the resulting mixture was heated under reflux for 2 hours. The reaction mixture was cooled, then neutralized, and concentrated. Ethyl acetate and water were added to the resulting residue, and the organic layer was collected by layer separation. The organic layer was washed with a saturated aqueous sodium chloride solution and dried with anhydrous magnesium sulfate. The desiccant was removed by filtration, and the solvent was distilled off from the filtrate to obtain a colorless oily compound mentioned above (5.35 g, 97.9%).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 2 hours
  3. temperatureThe reaction mixture was cooled
  4. concentrationconcentrated
  5. additionEthyl acetate and water were added to the resulting residue
  6. customthe organic layer was collected by layer separation
  7. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  8. dry with materialdried with anhydrous magnesium sulfate
  9. customThe desiccant was removed by filtration
  10. distillationthe solvent was distilled off from the filtrate
  11. customto obtain a colorless oily compound

Sources & evidence

ORD record
ord-af14abd3fb2e4fd3a5ec9b53e80de393
Source dataset
uspto-grants-2003_11
Patent number
US06642395B1

Reaction notes

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