Dibenzyl ketone

Dibenzyl ketone
IUPAC name 1,3-diphenylpropan-2-one
Identifiers
CAS number	102-04-5 Y
PubChem	7593
ChemSpider	21105887 Y
EC number	203-000-0
Jmol-3D images	Image 1
SMILES O=C(Cc1ccccc1)Cc2ccccc2
InChI InChI=1S/C15H14O/c16-15(11-13-7-3-1-4-8-13)12-14-9-5-2-6-10-14/h1-10H,11-12H2 Y Key: YFKBXYGUSOXJGS-UHFFFAOYSA-N Y InChI=1/C15H14O/c16-15(11-13-7-3-1-4-8-13)12-14-9-5-2-6-10-14/h1-10H,11-12H2 Key: YFKBXYGUSOXJGS-UHFFFAOYAS
Properties
Molecular formula	C15H14O
Molar mass	210.27 g mol−1
Appearance	light yellow solid
Density	1.069 g/cm3
Melting point	32–34 °C
Boiling point	330 °C
Hazards
Flash point	149.4 °C; 300.9 °F; 422.5 K
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Dibenzyl ketone, or 1,3-diphenylacetone, is an organic compound composed of two benzyl groups attached to a central carbonyl group. This results in the central carbonyl carbon atom being electrophilic and the two adjacent carbon atoms slightly nucleophilic. For this reason, dibenzyl ketone is frequently used in an aldol condensation reaction with benzil (a dicarbonyl) and base to create tetraphenylcyclopentadienone.

Preparation

Phenylacetone self condenses to form dibenzyl ketone.

phenylacetic acid is reacted with acetic anhydride and anhydrous potassium acetate and refluxed for two hours at 140−150 °C the mixture is distilled slowly so that the distillate is mostly acetic acid, from 45 minutes into the distillation carbon dioxide is released, the distillation takes 75 minutes, carbon dioxide is still being evolved when distillation is stopped the resultant liquid is a mixture of dibenzyl ketone and minor impurities, note if this mixture is heated above 200−205 °C resinification occurs with a decrease in the yield of the ketone.