Studies on 4, 4' -Dihydroxydiphenyl Methane

Chemistry Department, Faculty of Science, M.S. University of Baroda, Baroda-2.

Manuscript received 19 August 1971, accepted for publication, 7 February 1972

4,4'-Dihyd-roxydiphenyl methane with ethyl acetoacetate gave bi(4-methyl-6-coumarinyl1 methane. The benzoyl derivative of 3,3'-diacetyl-4,4'-dihydroxy-diphenyl methane gave methylene his (1$-diketone) on Baker-Venkataraman transformation which was cyclized to hi (6-flavonol)methane. The above hydroxy acetyl derivative gave bi(4-hydroxy-6- cmunarinyl) methane with ethyl carbonate. Bi(3-methyl-5-benzo-uranyl) methane is also synthesized from the diacetyl derivative.

4,4'-Didihydroxydipbenyl methane did not give a pure product on chloromethylation but its dimethyl ether gave the 3,3 1-di(chloro:rnethyl) derivative which has been converted in.to the diacetoxymethyl) and the di(cyanomethyl) derivatives and into the difornlyl derivative.

3,3' -Diformyl-4,4' -dihyd-roxydiphenyl Jnethane was condensed with diethyl Bromo malonate and bi(5-benzofuranyl) Jnethane was synthesized. Bi(3-carbethoxy-6-coumarinyl) methane was obtained on the condensation of the difor.myl derivative with diethyl malonate. This on hydrolysis and decarboxylation gave bi(6-coumarinyl) methane which was also obtained by Perkin acetylation of 3,3'-for.uyl-4.4'-dihydroxy-diphenyl .nethane.