Potassium Carbonate → (S)-Glycidyl-3-benzyloxyphenol

HRID 1519

Reaction equation

HRID 1519 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([OH:15])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:22](OS(C1C=CC=C([N+]([O-])=O)C=1)(=O)=O)[C@H:23]1[O:25][CH2:24]1>CC(C)=O>[CH2:22]([C:10]1[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:14][CH:13]=[CH:12][C:11]=1[OH:15])[C@@H:23]1[O:25][CH2:24]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 138048Benzyl 3-hydroxyphenyl etherHCID 146490Benzenesulfonic acid, 3-nitro-, (2S)-2-oxiranylmethyl ester

Product 1

HCID 54485604(S)-Glycidyl-3-benzyloxyphenol

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

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.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 15 mins
  3. temperaturethe reaction mixture was heated
  4. temperatureunder reflux for 23 hours
  5. temperatureAfter cooling the reaction mixture
  6. filtrationwas filtered
  7. customthe solvent was evaporated
  8. customThe residue was partitioned between ethyl acetate and water
  9. washwashed with water and brine
  10. customdried
  11. customevaporated

Sources & evidence

ORD record
ord-7a6d0a34d26147ccbbd1b4a703979302
Source dataset
uspto-grants-1998_03
Patent number
US05726165

Linked notes

Loading…