1'-ацетонафтон

Химические свойства

clear pale yellow to yellow liquid

Использование

1'-Acetonaphthone is used in the preparation of S(-)-1-(1'-naphthyl) ethanol, an important synthetic intermediate of mevinic acid analog.

Общее описание

Stereoselective reduction of 1-acetonapthone in aqueous media by whole cells of Geotrichum candidum has been investigated in various organic co-solvents. Magnetic field effects on the photoinduced electron-transfer reaction between 1-acetonaphthone and diphenylamine in micellar solution have been studied by laser flash photolysis.

Профиль безопасности

Moderately toxic by ingestion. A skin irritant. A combustible liquid. When heated to decomposition it emits acrid smoke and irritating fumes

Синтез

1'-Acetonaphthone is produced from Naphthalene with Acetylchloride and Aluminum chloride (Friedel-Craft's synthesis) using Carbon disulfide as a solvent in order to favour the formation of alpha-isomer.

Методы очистки

If the NMR spectrum indicates the presence of impurities, probably 2-acetylnaphthalene, convert the substance to its picrate by dissolving in *benzene or EtOH and adding excess of saturated picric acid in these solvents until separation of picrates is complete. Recrystallise the picrate till the melting point is 118o. Decompose the picrate with dilute NaOH and extract with Et2O. Dry the extract (Na2SO4), filter, evaporate and distil the residue. The 2,4-dinitrophenylhydrazone crystallises from EtOH and has m 259o. [Stobbe & Lenzer Justus Liebigs Ann Chem 380 95 1911, Williams & Osborne J Am Chem Soc 61 3438 1939, Beilstein 7 IV 1292.]