Acetonitrile → 3-Hydroxy3, 3-di(4-biphenylyl) propionitrile

Participants

Reaction Steps

Di-4-biphenylyl ketone was reacted with acetonitrile in benzene in the presence of sodamide by the method of Lettre and Wick (Annalen, 1957, 603, 194) to give 3-hydroxy-3, 3-di(4-biphenylyl) propionitrile, m.p. 168°-170° C, after recrystallisation from benzene. The nitrile (8.0 g.) dissolved in a mixture of tetrahydrofuran (80 ml.) and ether (80 ml.) was added over 30 minutes at room temperature under nitrogen to a stirred suspension of lithium aluminium hydride (2.88 g.) in ether (75 ml.). After stirring a further hour the mixture was decomposed by addition of water (2.8 ml.) and aqueous N sodium hydroxide (12 ml.) After filtration, the organic layer was separated and evaporated to give a solid which recrystallised from benzene/light petroleum (b.p. 80°-100° C), gave 1,1-di(4-biphenylyl)-3-aminopropan-1-ol, prisms, m.p. 176°-8° C,λmax (ethanol) = 260 nm. The carbinol (6.5 g.) boiled under reflux for 1 hour with glacial acetic acid (40 ml.) and concentrated hydrochloric acid (10 ml.) gave 1, 1-di-(4-biphenylyl)-3-aminoprop-1-ene hydrochloride, needles from n-propanol, m.p. 231°-232° C. The base, from ethanol, had m.p. 127°-8° C, λmax (ethanol) = 274 nm.

Provenance & Evidence