Reaktion #450186

Reaktionsgleichung

2-methyl-3-nitro-phenol

triphenylphosphine

chloroethanol

→

light yellow solid

Ausbeute 100.0%

1-(2-Chloroethoxy)-2-methyl-3-nitrobenzene

Ausbeute 100.0%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe solvent was removed
2. 2
   workup.DISSOLUTIONthe residue dissolved in 1:1 ethyl acetate-hexanes (150 mL)
3. 3
   FiltrationAfter 30 min the solid triphenylphosphine oxide was filtered
4. 4
   Sonstigethe solvent again removed
5. 5
   SonstigeThe crude product was purified by chromatography (20% ethyl acetate-hexanes)

Vorschrift

To a solution of 2-methyl-3-nitro-phenol (3.0 g, 19.6 mmol), triphenylphosphine (7.2 g, 27.4 mmol), and chloroethanol (1.89 g, 23.5 mmol) in anhydrous tetrahydrofuran (70 mL) was slowly added a solution of diethylazidodicarboxylate (4.78 g, 27.4 mmol). After 1 h the reaction was complete and the solvent was removed and the residue dissolved in 1:1 ethyl acetate-hexanes (150 mL). After 30 min the solid triphenylphosphine oxide was filtered and the solvent again removed. The crude product was purified by chromatography (20% ethyl acetate-hexanes) to afford 4.2 g (100%) of a light yellow solid: mp 58°-59° C.

Quelle