Reacción #736897

Ecuación de reacción

nitrobenzene

2-hexadecanoyl naphthalene

naphthalene

aluminium chloride

nitrobenzene

→

2-hexadecyl naphthalene

2-Hexadecanoyl naphthalene

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONrather than a mixture of the 1- and 2-isomers
2. 2
   OtroThe compound obtained
3. 3
   workup.DISTILLATIONvacuum distilled
4. 4
   Otrofurther purified by column chromatography on an alumina column in petroleum ether

Procedimiento

2-hexadecyl naphthalene was prepared by the Wolff-Kishner reduction of 2-hexadecanoyl naphthalene using the Huaing-Minlon modification (Anderson JACS)(1953) p449). 2-Hexadecanoyl naphthalene was prepared by the Friedel-Craft's reaction between 2-hexadecanoyl chloride (palmitoyl chloride) and naphthalene in the presence of anhydrous aluminium chloride and nitrobenzene using the method of Buu-Hoi & Cagnint (Bull. Soc. Chim., 12 (1945) p307). The presence of nitrobenzene seems to ensure the formation of the 2-isomer rather than a mixture of the 1- and 2-isomers. The compound obtained was then vacuum distilled and further purified by column chromatography on an alumina column in petroleum ether. Its purity was confirmed by melting point and infra-red spectroscopy.

Fuente