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Studies on 4, 4' -Dihydroxydiphenyl Methane

Authors: S. P. PRAJAPATI; SURESH SETHNA;

Studies on 4, 4' -Dihydroxydiphenyl Methane

Abstract

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'-Dihydroxydiphenyl methane with ethyl acetoacetate gave bi(4-methyl-6-coumarinyl) methane. The benzoyl derivative of 3,3'-diacetyl-4,4'-dihydroxy-diphenyl methane gave a methylenebis (β-diketone) on Baker-Venkataraman transformation which was cyclised to hi (6-flavonyl)methane. The above hydroxy acetyl derivative gave bi(4-hydroxy-6- coumarinyl) methane with ethyl carbonate. Bi(3-methyl-5-benzofu-ranyl) methane is also synthesised 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(chloromethyl) derivative which has been converted into the diacetoxymethyl) and the di(cyanomethyl) derivatives and into the difomlyl derivative. 3,3' -Diformyl-4,4' -dihydroxydiphenyl methane was condensed with diethyl bromo malonate and bi(5-benzofuranyl) methane was synthesised. Bi(3-carbethoxy-6-coumarinyl) methane was obtained on 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'-diformyl-4,4'-dihydroxy-diphenyl methane.

Keywords

Dihyd-roxydiphenyl, Methane., Acetoacetate, coumarin derivative, chloromethylation, Hydroxy, Diacetoxymethyl

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