Abstract A number of new liquid crystalline compounds containing an α, β-unsaturated ketone or β-chloro ketone moiety in the side chain were synthesized. The key intermediates in the synthesis were 1-(4-hydroxy-phenyl)-2-octen-1-one and 3-chloro-1-(4-hydroxyphenyl) octan-1-one which were prepared from 5-(4-hydroxy-phenyl)-3-pentyl-4, 5-dihydroisoxazole and 3-hydroxy-1-(4-hydroxyphenyl) octan-1-one, respectively.