Hydrochloric Acid → 3-(2-Phenyl-vinyl)-benzyl alcohol

Participants

Reaction Conditions

Reaction Steps

10 g (0.03 mol) of 3-(2-phenyl-vinyl)-benzoic acid ethyl ester, dissolved in 50 ml of dry tetrahydrofuran, were added dropwise to 2.5 g of lithium aluminium hydride in 50 ml of anhydrous tetrahydrofuran at 25°-30° C., whilst stirring thoroughly. The reaction mixture was then subsequently stirred at 22° C. for 10 hours and then cooled to 0° C. and ice-water was added dropwise, whilst stirring, until no further evolution of hydrogen could be observed (60 ml). The precipitate which had formed was dissolved by adding 30 ml of concentrated hydrochloric acid dropwise, and the reaction mixture was then extracted twice with 100 ml of toluene each time. The organic phase was separated off and dried over sodium sulphate and the solvent was distilled off under a waterpump vacuum. Last residues of solvent were removed by subjecting the product to brief incipient distillation at a bath temperature of 60° C./1 mm Hg. 5 g (61% of theory) of 3-(2-phenyl-vinyl)-benzyl alcohol were obtained as a yellow oil with the refractive index nD22 : 1.6286 (isomer mixture with a cis proportion of about 90%). ##STR62##

Provenance & Evidence