Benzyl vinyl ether is prepared by the reaction of vinyl acetate and benzyl alcohol. The steps are as follows:
Benzyl alcohol (5.18 mL, 50.0 mmol) and vinyl acetate (9.22 mL, 100 mmol, 2.0 equiv) are added to a suspension of [Ir(cod)Cl]2 (336 mg, 0.500 mmol, 1 mol %) and Na2CO3 (3.18 g, 30.0 mmol, 0.6 equiv) in toluene (50 mL).
After stirring for 2 hours at 100° C., the mixture obtained is cooled down to ambient temperature and filtered on Celite.
The filtrate is concentrated under reduced pressure and the residue purified by flash chromatography on silica gel (petroleum ether/EtOAc: 98/2) in order to produce a yellow oil (5.15 g, 77%).
1H-NMR (CDCl3, 400 MHz) δ 7.39-7.29 (m, 5H), 6.57 (dd, J=14.3 Hz and J=6.8 Hz, 1H), 4.76 (s, 2H), 4.30 (dd, J=14.3 Hz and J=2.0 Hz, 1H), 4.08 (dd, J=6.8 Hz and J=2.0 Hz, 1H).
