Estragole → 2-((4-Methoxyphenyl)methyl)oxirane

HRID 33966

Reaktionsgleichung

Reaktionsgleichung von HRID 33966
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][CH:5]=1)[CH:2]=[CH2:3].ClC1C=C(C=CC=1)C(OO)=[O:17]>ClCCl>[CH3:11][O:10][C:7]1[CH:8]=[CH:9][C:4]([CH2:1][CH:2]2[CH2:3][O:17]2)=[CH:5][CH:6]=1

Komponenten

4

Edukt 2

HCID 8815EstragoleHCID 70297m-Chloroperbenzoic acid

Produkt 1

HCID 400042-((4-Methoxyphenyl)methyl)oxirane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirring solution of 4-allylanisole (3.1 g, 20.9 mmol) in 50 mL dichloromethane was added 3-chloroperoxybenzoic acid (80%, 6.7 g, 31.4 mmol) at room temperature. TLC (20:1 hexanes/ethyl acetate) showed no remaining allyl after 3 h. The precipitate was removed via filtration and washed with hexanes. The filtrate was purified on 40 g silica eluting with 0 to 10% ethyl acetate/hexanes to give the product. NMR CDCl3) d (1H, 2.55 ppm), m (2H, 2.7-2.8 ppm), dd (1H, 2.85 ppm), m (1H, 3.1 ppm), s (3H, 3.75 ppm), d (2H, 6.85 ppm), d (2H, 7.15 ppm).

Aufarbeitung

  1. customafter 3 h
  2. customThe precipitate was removed via filtration
  3. washwashed with hexanes
  4. customThe filtrate was purified on 40 g silica eluting with 0 to 10% ethyl acetate/hexanes
  5. customto give the product

Quellen und Nachweise

ORD-Eintrag
ord-a88c8ddbb315481cb31f45009fe4e6da
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07429594B2

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