92 ORGANIC SYNTHESES TETRAPHENYLCYCLOPENTADIENONE (Cyclopentadienone, tetrapheny!-) CsH{COCOCGHs + (CeHlsCHH,)CO SE Celle CoH [o, + 2820 CoH Colle i oO Submited by Jomy R, Jonson and Ouvee Gxvwarrs Checked by Nartaw L. Deaxe and Sroaer Havwooo. 1, Procedure Iw a $00-cc. round-bottomed flask, 21 g, (0.1 mole) of benzil (Org. Syn. Coll. Vol. 1, 1941, 87) and 21 g. (0.1 mole) of dibenzyl ketone (Note 1) are dissolved in 150 cc. of hot alcohol. ‘The flask is fitted with a reflux condenser, the temperature of the solution is, raised nearly to the boiling point, and a solution of 3 g. of potas- sium hydroxide in 15 cc. of alcohol is added slowly in two portions through the condenser. When the frothing has subsided the mix- ture is refluxed for fifteen minutes and then cooled to 0°. The dark crystalline product is filtered with suction and washed with three 10-cc. portions of 95 per cent alcohol. ‘The product melts at 218-20° and weighs 45-37 g. (91-96 per cent of the theoretical amount) (Note 2). 2. Notes 1. The dibenzyl ketone should melt at 34-35°. 2. ‘This product is suficiently pure for most purposes. Tt may be crystallized from a mixture of alcohol and benzene using 155~ 160 ce. solvent for 5 g. of tetraphenylcyclopentadienone; the melt- ing point of the recrystallized material is 219-220",‘TETRAPHENYLPHTHALIC ANHYDRIDE 93, 8, Methods of Preparation ‘Tetraphenyleyclopentadienone has been prepared by the ac- tion of phenylmagnesium bromide on benzaldiphenylmaleide,t and by reduction, dehydration, and oxidation of the methylene desoxybenzoin obtained by condensing formaldehyde with desoxy- benzoin* The present procedure is essentially that of Dilthey.* TETRAPHENYLPHTHALIC ANHYDRIDE (Phthalic anhydride, tetraphenyl-) Cols i; CHs 9 ane cuc€”—Catly7\~ De Hie Si aero SICK Caley, CoHs a CoHs No CoH Cols 0 0 catty ch Cotte Sch Cale | ++ 2HBr Ha LACK oH) CoHs 0 Sn 80 Submited by Onsven Gnenaurrs, Checked by Naruay L, Drake and Cuances M. Eaxen, 1. Procedure Av intimate mixture of 35 g. (0.094 mole) of tetrapbenyley- clopentadienone (p. 92) and 9.3 g. (0.095 mole) of maleic anhy- ride is placed in a 200-cc. round-bottomed flask (Note 1), and to ivis added 25 ce, of bromobenzene, After the mixture has been refluxed gently for three and one-half hours (Note 2), itis cooled “Lomenbein and Ulich, Ber. 8, 2662 (1925). ler and Scheel, Ata, 445, 266 1923) ilehey and Quint, J. prake, Cher. (2) 198, 146 (1950); Ger. pat, $75,887 (Fra. 29, $03 (1985); C.K 98,1386 (1934).