An organic compound ‘A’ $\left(C_9{H}_8{O}_2\right)$ does not decolorizes bromine water and evolves no gas with  $C{H}_{3}MgBr$, but gives orange precipitate with 2, 4 – dinitro phenyl hydrazine. ‘A’ on refluxing with dil. $H_{2}S{O}_4$  produces $B\left(C_9{H}_{10}{O}_3\right)$ which forms salt with NaOH and on treatment with $C{H}_{3}COC\ell$  yields $C_{13}{H}_{14}{O}_5$  . B is a non–resolvable compound which on heating with $N_2{H}_4/NaOH$  yields ‘C’ $\left(C_9{H}_{12}{O}_2\right)$  . ‘C’ on dehydrating with conc. $H_{3}P{O}_4$  yields ‘D’  $\left(C_9{H}_{10}O\right)$ as major product. ‘D’ on ozonolysis following by work–up with ${\left(C{H}_3\right)}_{2}S$ yields ‘E’ $\left(C_7{H}_6{O}_2\right)$  which can also be obtained by the action of phenol with alkaline solution of chloroform followed by acidification of product.