4-tert-Butylphenol → 4-tert-Butylphenyl glycidyl ether, (+)-

HRID 237729노트

반응식

HRID 237729 반응식
[CH2:1]([C@@H:3]1[O:5][CH2:4]1)Cl.[C:6]([C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1)([CH3:9])([CH3:8])[CH3:7].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:6]([C:10]1[CH:11]=[CH:12][C:13]([O:16][CH2:1][C@@H:3]2[CH2:4][O:5]2)=[CH:14][CH:15]=1)([CH3:9])([CH3:7])[CH3:8]

참가 물질

5

반응물 3

HCID 73934-tert-ButylphenolHCID 11430Potassium CarbonateHCID 2734062(-)-Epichlorohydrin

생성물 1

HCID 7193734-tert-Butylphenyl glycidyl ether, (+)-수율 67%

시약·촉매·용매 1

HCID 180Acetone용매

반응 조건

온도
45 °C

실험 절차

To a mixture of (R)-epichlorohydrin (12.4 g, 134 mmol) and 4-tert-butylphenol (10.0 g, 66.8 mmol) in acetone (50 ml) was added potassium carbonate (9.24 g, 66.8 mmol). The mixture was stirred at 45° C. for 96 hours. The reaction mixture was then concentrated to remove acetone. The residue was partitioned between ethyl acetate and water and extracted twice with ethyl acetate. The organic phases were combined and washed with water, brine, dried over sodium sulfate and concentrated under vacuum. The resulting residue was purified by flash chromatography (silica, methylene chloride/heptane) to give 9.18 g (67%) of (S)-2-(4-tert-butyl-phenoxymethyl)oxirane.

후처리

  1. concentrationThe reaction mixture was then concentrated
  2. customto remove acetone
  3. customThe residue was partitioned between ethyl acetate and water
  4. extractionextracted twice with ethyl acetate
  5. washwashed with water, brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under vacuum
  8. customThe resulting residue was purified by flash chromatography (silica, methylene chloride/heptane)

출처 및 근거

ORD 기록
ord-513245e328264cf5b9f40f2df61fdfd0
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642603B2

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