Reaction #1615

Reaction equation

3-benzyloxyphenol

potassium carbonate

(S)-Glycidyl-3-nitrobenzenesulphonate

→

title compound

(S)-Glycidyl-3-benzyloxyphenol

Solvents

acetone

Conditions

Workup

1. 1
   Temperaturewas heated
2. 2
   Temperatureunder reflux for 15 mins
3. 3
   Temperaturethe reaction mixture was heated
4. 4
   Temperatureunder reflux for 23 hours
5. 5
   TemperatureAfter cooling the reaction mixture
6. 6
   Filtrationwas filtered
7. 7
   Otherthe solvent was evaporated
8. 8
   OtherThe residue was partitioned between ethyl acetate and water
9. 9
   Washwashed with water and brine
10. 10
    Otherdried
11. 11
    Otherevaporated

Procedure

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