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).