Reaktion #363985

Reaktionsgleichung

hexaethylene glycol monobenzyl ether

NaH

triethylene glycol methyl tosyl ether

→

nonaethylene glycol benzyl methyl ether

Ausbeute 88.0%

Lösungsmittel

THF

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was refluxed under nitrogen overnight
2. 2
   Temperaturcooled to ambient temperature
3. 3
   Sonstigequenched with water (500 ml)
4. 4
   Extraktionextracted with diethyl ether (3×300 ml)
5. 5
   Trocknendried (sodium sulfate)
6. 6
   Einengenconcentrated in vacuo

Vorschrift

A solution of hexaethylene glycol monobenzyl ether from above (22.3 g) in anhydrous THF (100 ml) was added to a suspension of 50% NaH (3.5 g) in anhydrous THF (100 ml). The suspension was stirred at ambient temperature for 30 min and then a solution of triethylene glycol methyl tosyl ether from above (22.0 g) in THF (100 ml) was added dropwise. The mixture was refluxed under nitrogen overnight, cooled to ambient temperature, quenched with water (500 ml), and extracted with diethyl ether (3×300 ml). The ether extracts were combined, dried (sodium sulfate), and concentrated in vacuo to give nonaethylene glycol benzyl methyl ether as an oil (27 g, 88%), 1H-NMR (CDCl3) δ: 7.31 (m, 5, 5 phenyl CH), 4.54 (s, 2, benzyl CH2), 3.62-3.52 (m, 36, 18 CH2O), 3.35 (s, 3, CH3).

Quelle