Acetic Acid → 2-(3-Methoxyphenyl)oxirane

HRID 562943

Reaktionsgleichung

Reaktionsgleichung von HRID 562943
[CH:1]([C:3]1[CH:4]=[C:5]([O:9][CH3:10])[CH:6]=[CH:7][CH:8]=1)=[CH2:2].C(O)(=[O:13])C.BrN1C(=O)CCC1=O.[OH-].[Na+]>O1CCOCC1.O>[CH3:10][O:9][C:5]1[CH:4]=[C:3]([CH:1]2[CH2:2][O:13]2)[CH:8]=[CH:7][CH:6]=1

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 67184N-bromobutanimideHCID 5841461-Ethenyl-3-methoxybenzene

Produkt 1

HCID 979032-(3-Methoxyphenyl)oxiraneAusbeute 100,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a solution of 3-vinylanisole (5.0 g, 37.0 mmol) and acetic acid (2.1 mL, 37.0 mmol) in dioxane (33 ml) and H2O (78 ml) at 0° C. was added N-bromosuccinimide (7.30 g, 41.0 mmol) in three portions. The reaction was allowed to warm to R.T. and then 2M NaOH (50 ml) was added. The reaction was left to stir at RT overnight. The reaction mixture was then partitioned between water and EtOAc, and the aqueous phase was extracted with EtOAc. The combined organic phases washed with brine, dried (Na2SO4), filtered and evaporated in vacuo to give 5.60 g (100%) of the title compound as a slightly tinted oil.

Aufarbeitung

  1. waitThe reaction was left
  2. customThe reaction mixture was then partitioned between water and EtOAc
  3. extractionthe aqueous phase was extracted with EtOAc
  4. washThe combined organic phases washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-fa14735825fc4d20ba49a5cdebd6088c
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08067450B2

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