Réaction #1615

ord-7a6d0a34d26147ccbbd1b4a703979302

Équation de réaction

Oc1cccc(OCc2ccccc2)c1
3-benzyloxyphenol
O=C([O-])[O-].[K+].[K+]
potassium carbonate
O=[N+]([O-])c1cccc(S(=O)(=O)OC[C@@H]2CO2)c1
(S)-Glycidyl-3-nitrobenzenesulphonate
Oc1cccc(OCc2ccccc2)c1C[C@H]1CO1
title compound
Oc1cccc(OCc2ccccc2)c1C[C@H]1CO1
(S)-Glycidyl-3-benzyloxyphenol

Solvants

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Températurewas heated
  2. 2
    Températureunder reflux for 15 mins
  3. 3
    Températurethe reaction mixture was heated
  4. 4
    Températureunder reflux for 23 hours
  5. 5
    TempératureAfter cooling the reaction mixture
  6. 6
    Filtrationwas filtered
  7. 7
    Autrethe solvent was evaporated
  8. 8
    AutreThe residue was partitioned between ethyl acetate and water
  9. 9
    Lavagewashed with water and brine
  10. 10
    Autredried
  11. 11
    Autreevaporated

Mode opératoire

A mixture of 3-benzyloxyphenol (900 mg, 4.5 mMol) and potassium carbonate (1.87 g, 13.5 mMol) in acetone (45 ml) was heated under reflux for 15 mins. (S)-Glycidyl-3-nitrobenzenesulphonate (1.0 g, 4.5 mMol) was added and the reaction mixture was heated under reflux for 23 hours. After cooling the reaction mixture was filtered and the solvent was evaporated. The residue was partitioned between ethyl acetate and water. The organic fractions were combined, washed with water and brine, dried and evaporated to give the title compound as an oil.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US05726165uspto-grants-1998_03