Reaktion #516194

Reaktionsgleichung

ethyl acetate

vinylbenzylchloride

Potassium tert-butoxide

1,3-propanediol

→

title compound

Ausbeute 81.0%

3-(vinylbenzyloxy)-1-propanol

Ausbeute 81.0%

Lösungsmittel

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction was heated
2. 2
   Temperaturat reflux overnight
3. 3
   Sonstigethe tetrahydrofuran was removed in vacuo
4. 4
   WaschenThe organic phase was washed with water
5. 5
   Trocknendried (magnesium sulfate)
6. 6
   Einengenconcentrated in vacuo
7. 7
   Sonstigeto give a liquid
8. 8
   SonstigeThe liquid was purified by column chromatography over silica gel (eluent 3:1

Vorschrift

Potassium tert-butoxide (23.07 g, 0.206 mol) was added to a stirred solution of 1,3-propanediol (44.92 g, 0.591 mol) in dry tetrahydrofuran (400 ml) under an atmosphere of nitrogen. The reaction mixture was stirred for 15 min then a solution of vinylbenzylchloride (mixture of meta and para isomers) (30.00 g, 0.197 mol) in dry tetrahydrofuran (100 ml) was added dropwise over 30 min. The reaction was heated at reflux overnight then the tetrahydrofuran was removed in vacuo and the residue taken-up in water (400 ml) and diethyl ether (400 ml). The organic phase was washed with water, dried (magnesium sulfate) and concentrated in vacuo to give a liquid. The liquid was purified by column chromatography over silica gel (eluent 3:1:petrol ether/ethyl acetate, then ethyl acetate) to give the title compound (30.59 g, 0.159 mol, 81%) as a straw colored liquid.

Quelle