Toluene → (S)-(+)-1-Phenyl-1,2-ethanediol 2-tosylate

HRID 479002Notes

Reaction equation

HRID 479002 reaction equation
C1(C)C=CC=CC=1.[C:8]1([CH3:32])[CH:13]=[CH:12][C:11]([S:14]([O:17][CH2:18][C@H:19]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[O:20]C(OC)(C)C)(=[O:16])=[O:15])=[CH:10][CH:9]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[C:8]1([CH3:32])[CH:9]=[CH:10][C:11]([S:14]([O:17][CH2:18][C@H:19]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[OH:20])(=[O:16])=[O:15])=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 521998p-Toluenesulfonic acid monohydrateHCID 87788494HCID 87788494, compound

Product 1

HCID 7019623(S)-(+)-1-Phenyl-1,2-ethanediol 2-tosylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

Into toluene (10 ml) were added (S)-2-phenyl-2-(1-methoxy-1-methylethyloxy)ethyl p-toluenesulfonate (3.0 g), p-toluenesulfonic acid monohydrate (1.7 g) and methanol (0.5 g), and the resulting mixture was stirred at 50° C. for 1 hour. The reaction mixture was washed with a saturated aqueous sodium hydrogen carbonate solution, then with a saturated aqueous sodium chloride solution, and dried with anhydrous magnesium sulfate. The desiccant was filtered off and then the solvent was distilled off under reduced pressure to obtain a colorless oily compound mentioned above (2.1 g, 88.0%).

Workup

  1. washThe reaction mixture was washed with a saturated aqueous sodium hydrogen carbonate solution
  2. dry with materialwith a saturated aqueous sodium chloride solution, and dried with anhydrous magnesium sulfate
  3. filtrationThe desiccant was filtered off
  4. distillationthe solvent was distilled off under reduced pressure
  5. customto obtain a colorless oily compound

Sources & evidence

ORD record
ord-f761ef00ff4044429920e93b71595ccc
Source dataset
uspto-grants-2003_11
Patent number
US06642395B1

Reaction notes

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