Reaktion #426186

Reaktionsgleichung

(2-nitrophenyl)methanol

NaOH

Me2SO4

→

1-(methoxymethyl)-2-nitrobenzene

Ausbeute 91.4%

Lösungsmittel

DCM

DCM

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture stirred vigorously for 20 hours at ambient temperature
2. 2
   Sonstigewas separated
3. 3
   Waschenwashed with brine
4. 4
   Trocknendried (sodium sulfate)
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated under reduced pressure
7. 7
   SonstigeThe residue was purified by flash chromatography on silica gel (5:1 hexane/ethyl acetate)

Vorschrift

To a solution of (2-nitrophenyl)methanol (5.13 g, 33.50 mmol) in DCM (75 mL) was added 3.35 N NaOH (75 mL, 251.2 mmol) in water at ambient temperature and stirred at ambient temperature for 10 minutes. Me2SO4 (6.38 ml, 67.0 mmol) and tetrabutylammonium hydrogen sulfate (0.57 g, 1.68 mmol) were added and the mixture stirred vigorously for 20 hours at ambient temperature. The reaction mixture was diluted with DCM (100 mL) and organic layer was separated, washed with brine, dried (sodium sulfate), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (5:1 hexane/ethyl acetate) to give 1-(methoxymethyl)-2-nitrobenzene (5.12 g, 91.4%) as an oil.

Quelle