1-(5-chloro-2-hydroxyphenyl)-ethanone (1a) was prepared from 2-chlorophenol through multi-step reaction. Compound (1a) reacts with different aryl aldehyde in the presence of NaOH (40%) to gives 1-(5-chloro-2- hydroxyphenyl)-3-(4-substitutedphenyl)-prop-2-en-1-one (2a-e). 4-(5-chloro-2-hydroxy phenyl)-6-(4-substituted phenyl)-pyrimidin-2-(1H)-one (3a-e) and 4-(5-chloro-2-hydroxyphenyl)-6-(4-substitutedphenyl)-pyrimidin-2-(1H)- thione (4a-e) was achieved through cyclisation of 1-(5-chloro-2-hydroxyphenyl)-3-(4-substitutedphenyl)-prop-2-en- 1-one (2a-e) with urea and thiourea in ethanol containing catalytic amount of KOH respectively. All the synthesized compounds were characterized on the basis of spectral data.