Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Naphthalene | HCID 931 | — |
| Reactant | Nitrobenzene | HCID 7416 | — |
| Reactant | Aluminum(III) Chloride | HCID 6451240 | — |
| Reactant | HCID 21713270 | HCID 21713270 | — |
| Product | 1-(2-Napthyl)hexadecane | HCID 12277389 | — |
| Product | HCID 21713270 | HCID 21713270 | — |
Reaction Steps
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.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06270653B1 |
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| Source dataset | uspto-grants-2001_08 |
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| ORD ID | ord-060721eba2a3439bbaf18fb7c1acf0f9 |
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| Source note | uspto-grants-2001_08 |
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