Dibenzyl ketone

Dibenzyl ketone
Names
	IUPAC name 1,3-diphenylpropan-2-one
Identifiers
CAS Number	102-04-5 ;
3D model (JSmol)	Interactive image;
ChemSpider	21105887 ;
ECHA InfoCard	100.002.728
EC Number	203-000-0;
PubChem CID	7593;
UNII	9Y07G5UDKQ ;
CompTox Dashboard (EPA)	DTXSID5059244 ;
	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 Key: YFKBXYGUSOXJGS-UHFFFAOYSA-N ; 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;
	SMILES O=C(Cc1ccccc1)Cc2ccccc2;
Properties
Chemical formula	C15H14O
Molar mass	210.276 g·mol−1
Appearance	light yellow solid
Density	1.069 g/cm3
Melting point	32 to 34 °C (90 to 93 °F; 305 to 307 K)
Boiling point	330 °C (626 °F; 603 K)
Magnetic susceptibility (χ)	-131.7·10−6 cm3/mol
Hazards
Flash point	149.4 °C (300.9 °F; 422.5 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	verify (what is ?)
	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. Vera Bogdanovskaia is credited with the classification of dibenzyl ketone.

Preparation

Phenylacetone self condenses to form dibenzyl ketone.

One method is[1] where 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. Carbon dioxide is released in this reaction. The resultant liquid is a mixture of dibenzyl ketone and minor impurities. Heating the mixture above 200−205 °C leads to resinification with a decrease in the yield of the ketone.

References

Hurd, Charles D.; Thomas, Charles L. (1936). "Preparation of Dibenzyl Ketone and Phenylacetone". J. Am. Chem. Soc. 58 (7): 1240. doi:10.1021/ja01298a043.

This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.

[1] Hurd, Charles D.; Thomas, Charles L. (1936). "Preparation of Dibenzyl Ketone and Phenylacetone". J. Am. Chem. Soc. 58 (7): 1240. doi:10.1021/ja01298a043.