Sodium Hydroxide → (R)-(+)-3-Chlorostyrene oxide

HRID 479007Notes

Reaction equation

HRID 479007 reaction equation
CS(O[CH2:6][C@@H:7]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[CH:10]=1)[OH:8])(=O)=O.[OH-].[Na+]>CS(C)=O>[Cl:15][C:11]1[CH:10]=[C:9]([CH:14]=[CH:13][CH:12]=1)[C@H:7]1[O:8][CH2:6]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15442724HCID 15442724, compound

Product 1

HCID 10898919(R)-(+)-3-Chlorostyrene oxide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Into dimethyl sulfoxide (30 ml) were added (R)-2-(3-chlorophenyl)-2-hydroxyethyl methanesulfonate obtained in 2) above (10 g) and, under ice-cooling, a 5N aqueous NaOH solution (15 ml), and then the resulting mixture was stirred at the same temperature for 12 hours. The reaction mixture was added into ice water and extracted with 50% diethyl ether/pentane. The organic layer was washed with a saturated aqueous sodium chloride solution and then dried with anhydrous magnesium sulfate. The desiccant was filtered off, then the solvent was distilled off under reduced pressure, and the oily substance obtained was distilled under reduced pressure to obtain a colorless oily compound mentioned above (3.62 g, 76.5%). The optical purity of the product obtained was 97.5% e.e. as determined by HPLC.

Workup

  1. customobtained in 2) above (10 g)
  2. temperatureunder ice-cooling
  3. extractionextracted with 50% diethyl ether/pentane
  4. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  5. dry with materialdried with anhydrous magnesium sulfate
  6. filtrationThe desiccant was filtered off
  7. distillationthe solvent was distilled off under reduced pressure
  8. customthe oily substance obtained
  9. distillationwas distilled under reduced pressure
  10. customto obtain a colorless oily compound
  11. customThe optical purity of the product obtained

Sources & evidence

ORD record
ord-165b827cb0f54187ac74955e03728e7e
Source dataset
uspto-grants-2003_11
Patent number
US06642395B1

Reaction notes

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