Aluminium lithium hydride → 3-(4'-Chloro-[1,1'-biphenyl]-4-yl)-butenol

Participants

Reaction Conditions

Reaction Steps

To an ice cooled slurry of LiAlH4 (1.4 g) in dry ether (200 ml) was added a solution of ethyl 3-(4′-chloro-[1,1′-biphenyl]-4-yl)-but-2-enoate (3g, 2.8 g) in dry ether (50 ml) dropwise. The reaction mixture was stirred for 2 h at 0° C. The reaction mixture was quenched with water. A solution of 10% NaOH was added and the ether layer was decanted. The precipitate was washed with ether and the combined ether extract was concentrated. The crude product was chromatographed on silica gel to give 1.8 g (75% yield) of 3-(4′-chloro-[1,1′-biphenyl]-4-yl)-butenol (4g, formula 4, R=p-Cl—C6H4) m.p. 130-132° C.

Provenance & Evidence