Phenylacetaldehyde → Benzene, [1-[(trimethylsilyl)oxy]ethenyl]-

Participants

Reaction Steps

A mixture of 30.0 g (0.25 mol) of phenylacetaldehyde, 32.6 g (0.3 mol) of trimethylchlorosilane, 60.6 g (0.6 mol) of triethylamine, and 100 ml of N,N-dimethylformamide was refluxed overnight, cooled and diluted with 200 ml of pentane. The mixture was washed successively with cold 5% aqueous sodium bicarbonate, 1.5 N hydrochloric acid, and 5% aqueous sodium bicarbonate, dried (over MgSO4), and then distilled to give 21.15 g of α-trimethylsiloxystyrene as a colorless liquid: bp 80°-83.5° C. (3.8 mm); 1H NMR (CDCl3) δ 0.07 ppm (s, 9H), 5.87 ppm (d,J=12 Hz, 1H), 6.80 ppm (d,J=12 Hz, 1H) and 7.03 ppm (m, 5H).

Provenance & Evidence