Monobenzone → (S)-Glycidyl-4-benzyloxyphenol

HRID 1520

반응식

HRID 1520 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 54047008(S)-Glycidyl-4-benzyloxyphenol

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f128083fd7554ead9f40eeecd8845c28
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05726165

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