Reaktion #46735

Reaktionsgleichung

2-hydroxyoctyloxy-benzonitrile

sodium azide

triethylamine hydrochloride

NaOH

→

5-Octyloxy-2-(1H-tetrazol-5-yl)-phenol

Lösungsmittel

H2O

toluene

EtOAc

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe precipitate formed
2. 2
   SonstigeThe organic phase was isolated
3. 3
   Extraktionextracted with 4 M NaOH (aq)
4. 4
   Sonstigethe precipitate formed
5. 5
   Sonstigeisolated by filtration
6. 6
   Sonstigeto yield 240 mg (82%) as a purple solid
7. 7
   Sonstigeafter drying

Vorschrift

A slurry of 2-hydroxyoctyloxy-benzonitrile (247 mg; 1 mmol), sodium azide (195 mg; 3 mmol), triethylamine hydrochloride (411 mg; 3 mmol) was refluxed in toluene (5 mL) under N2 for 4 hours after which time the reaction mixture was poured onto H2O 0 (10 mL). The precipitate formed was dissolved by addition of 10 M NaOH (aq) and EtOAc. The organic phase was isolated and extracted with 4 M NaOH (aq). The combined aqueous phases was acidified using 12 M HCl (aq) and the precipitate formed isolated by filtration to yield 240 mg (82%) as a purple solid after drying. Mp. 142-146° C. MS (Direct; Cl): 291 (MH+).

Quelle