Monobenzone → (S)-Glycidyl-4-benzyloxyphenol

HRID 1520

Reaction equation

HRID 1520 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=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:11]1[CH:10]=[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:14]=[CH:13][C:12]=1[OH:15])[C@@H:23]1[O:25][CH2:24]1

Participants

5

Reactant 3

HCID 7638MonobenzoneHCID 11430Potassium CarbonateHCID 146490Benzenesulfonic acid, 3-nitro-, (2S)-2-oxiranylmethyl ester

Product 1

HCID 54047008(S)-Glycidyl-4-benzyloxyphenol

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4-benzyloxyphenol (2.0 g, 10 mMol) and potassium carbonate (4.14 g, 30 mMol) in acetone (50 ml) was heated under reflux for 15 mins. (S)-Glycidyl-3-nitrobenzenesulphonate (2.23 g, 10 mMol) was added and the reaction mixture was heated under reflux for 18 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 18 hours
  5. temperatureAfter cooling
  6. filtrationthe reaction mixture was 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-f128083fd7554ead9f40eeecd8845c28
Source dataset
uspto-grants-1998_03
Patent number
US05726165

Linked notes

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