Benzophenone → Benzene, 1,1'-(1,6-heptadienylidene)bis-

HRID 2232695Notes

Reaction equation

C(C1C=CC=CC=1)(=O)C1C=CC=CC=1.[C:15]1([C:21]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[CH:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[C:15]1([C:21]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)=[CH:22][CH2:23][CH2:24][CH2:25][CH:26]=[CH2:27])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

Reactant 2

HCID 3102Benzophenone

HCID 2986681,1-Diphenyl-1-heptene

Product 1

HCID 11021254Benzene, 1,1'-(1,6-heptadienylidene)bis-Yield 71%

Procedure

In a reaction conducted in an analogous manner to Example 4, the reagent from Example 2 converted benzophenone into 1,1-diphenyl-1-heptene in a 71% yield. This product could easily be separated from reduction products by column chromatography on silica gel using hexane as the eluent, or even by simple distillation. This hydrocarbon was identified by spectral comparison with an authentic sample that was obtained by the partial reduction of known 1,1-diphenyl-1,6-heptadiene (J. J. Eisch et al., J. Am. Chem. Soc., 1979, 101: 1148).

Workup

customThis product could easily be separated from reduction products by column chromatography on silica gel
distillationeven by simple distillation

Sources & evidence

ORD record: ord-c56f279c4b754bc0811128ed05757f25
Source dataset: uspto-grants-1988_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04788368

Reaction notes

Loading…