Toluene → HCID 22852268, compound

HRID 478995Notes

Reaction equation

HRID 478995 reaction equation
[C:1]1(C)C=CC=CC=1.[Cl:8][C:9]1[CH:19]=[CH:18][C:12]([C@@H:13]([OH:17])[C:14]([OH:16])=[O:15])=[CH:11][CH:10]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[CH3:1][O:15][C:14](=[O:16])[C@@H:13]([C:12]1[CH:18]=[CH:19][C:9]([Cl:8])=[CH:10][CH:11]=1)[OH:17]

Participants

5

Reactant 3

HCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 785085(2R)-(4-Chlorophenyl)(hydroxy)acetic acid

Product 1

HCID 22852268HCID 22852268, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Into toluene (20 ml) were added methanol (3.0 g), (R)-4-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 washed with a saturated aqueous sodium hydrogen carbonate solution, and then the organic layer was washed with a saturated aqueous sodium chloride solution and dried with anhydrous magnesium sulfate. The desiccant was filtered off and the solvent was distilled off to obtain a colorless oily compound mentioned above (5.23 g, 97.5%).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 2 hours
  3. temperatureThe reaction mixture was cooled
  4. washwashed with a saturated aqueous sodium hydrogen carbonate solution
  5. washthe organic layer was washed with a saturated aqueous sodium chloride solution
  6. dry with materialdried with anhydrous magnesium sulfate
  7. filtrationThe desiccant was filtered off
  8. distillationthe solvent was distilled off
  9. customto obtain a colorless oily compound

Sources & evidence

ORD record
ord-98b2a954c50a41d8a66f65d6f28679fe
Source dataset
uspto-grants-2003_11
Patent number
US06642395B1

Reaction notes

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