p-Toluenesulfonic acid → (R)-Methyl 2-(3-chlorophenyl)-2-hydroxyacetate

HRID 478993Notes

Reaction equation

HRID 478993 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[C@@H:5]([OH:9])[C:6]([OH:8])=[O:7].[C:13]1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[CH3:13][O:7][C:6](=[O:8])[C@@H:5]([C:4]1[CH:10]=[CH:11][CH:12]=[C:2]([Cl:1])[CH:3]=1)[OH:9]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 2733127(R)-2-(3-Chlorophenyl)-2-hydroxyacetic acid

Product 1

HCID 15606324(R)-Methyl 2-(3-chlorophenyl)-2-hydroxyacetate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Into methanol (20 ml) were added (R)-3-chloromandelic 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 then dried with anhydrous magnesium sulfate. The desiccant was filtered off and then the solvent was distilled off to obtain a colorless oily compound mentioned above (5.27 g, 98.3%).

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. filtrationThe desiccant was filtered off
  10. distillationthe solvent was distilled off
  11. customto obtain a colorless oily compound

Sources & evidence

ORD record
ord-001f1fb4da98422885262d5473d04cdb
Source dataset
uspto-grants-2003_11
Patent number
US06642395B1

Reaction notes

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