B-Phenylethyl alcohol has been synthesized from styrene through its conversion into styrene bromohydrin
which was dehydrobrominated to its epoxide and followed by hydrogenation. An aqueous solution of 105g. NaClO3 in 225ml. H2O and a mixed solution of 360 g. NaBr in 750 ml. H2O and dilute H2SO4 were added simultaneously into 210g. of styrene during 3.5-4 hrs. at 90-95℃ with vigorous stirring. After completing the reaction
the organic layer was separated and washed with water and dilute soda solution successively. The separated oil
distilled under vaccum
gave an yield of 80-85% styrene bromohydrin
b. p. 106-111℃/2-3 mm.
nD23.5 1.5770. Treating it with slight excess of a dilute solution of NaOH at 60-65℃
for 3-4 hrs. gave styrene oxide
b. p. 60-65℃/3-4 mm. nD22 1.5350
d1G1G 1.055
80-85% in yields
100 g. of styrene oxide
dissolved in 200 ml. ethyl alcohol
containing 3.3 g. NaOH was hydrogenated in the presence of Raney Ni catalyst under 3 atmosphere at room temperature to give β-phenylethyl alcohol