Reaktion #48623

Reaktionsgleichung

3-(1-hydroxy-2-nitroethyl)-phenol

18-Crown-6

potassium fluoride

acetic anhydride

→

desired compound

Acetic acid 3-(2-nitrovinyl)-phenyl ester

Lösungsmittel

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturCool in an ice bath
2. 2
   workup.STIRRINGstir for 15 minutes
3. 3
   SonstigeDecant
4. 4
   Extraktionextract the aqueous with ethyl acetate (twice)
5. 5
   WaschenCombine extracts with the solid, wash with water (twice), saturated aqueous sodium chloride (twice),
6. 6
   Trocknendry (magnesium sulfate)
7. 7
   Filtrationfilter
8. 8
   Einengenconcentrate
9. 9
   Sonstigepurify
10. 10
    Waschen(silica gel chromatography, eluting with 25:75 hexanes:dichloromethane to 100% dichloromethane)

Vorschrift

Add 3-(1-hydroxy-2-nitroethyl)-phenol (22.3 g, 121.8 mmol), 18-Crown-6 (3.3 g, 12.5 mmol), potassium fluoride (spray-dried) (7.1 g, 141 mmol) to acetic anhydride (115 mL, 1.218 mol). Stir for 1 hour. Cool in an ice bath and pour into ice water (400 mL) and stir for 15 minutes. Decant and extract the aqueous with ethyl acetate (twice). Combine extracts with the solid, wash with water (twice), saturated aqueous sodium chloride (twice), dry (magnesium sulfate), filter, concentrate and purify (silica gel chromatography, eluting with 25:75 hexanes:dichloromethane to 100% dichloromethane) to give the desired compound as an orange oil (25.56 g, 91%).

Quelle