p-Toluenesulfonic acid → Ethyl 3-(4'-chloro-[1,1'-biphenyl]-4-yl)-but-2-enoate

Participants

Reaction Steps

To a solution of crude ethyl 3-hydroxy-3-(4′-chloro-[1,1′-biphenyl]-4-yl)-butanoate (2g) in benzene (200 ml) was added p-toluenesulfonic acid (3 gm) and was refluxed for 3 h 30 minutes. The reaction mixture was cooled, neutralized with NaHCO3 solution, diluted with water and organic layer was extracted. Organic layer was washed with water, dried (NaHCO3) and concentrated. Crude product was purified by column chromatography on silica gel to furnish 5.27 g (47.=91% yield) of ethyl 3-(4′-chloro-[1,1′-biphenyl]-4-yl)-but-2-enoate (3g, formula 3, R=p-Cl—C6H4) m.p. 91-94° C.

Provenance & Evidence