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

HRID 237729ノート

反応式

HRID 237729 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

反応条件

温度
45 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-513245e328264cf5b9f40f2df61fdfd0
出典データセット
uspto-grants-2014_02
特許番号
US08642603B2

反応ノート

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