Naphthalene → 1-(2-Napthyl)hexadecane

HRID 649715Notes

Reaction equation

HRID 649715 reaction equation
[C:1]([C:18]1[CH:27]=[CH:26][C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=1)(=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].C1C2C(=CC=CC=2)C=CC=1.[Cl-].[Al+3].[Cl-].[Cl-].[N+](C1C=CC=CC=1)([O-])=O>>[CH2:1]([C:18]1[CH:27]=[CH:26][C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[C:1]([C:18]1[CH:27]=[CH:26][C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=1)(=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

6

Reactant 4

HCID 931NaphthaleneHCID 7416Nitrobenzene2×HCID 6451240Aluminum(III) ChlorideHCID 21713270HCID 21713270, compound

Product 2

HCID 122773891-(2-Napthyl)hexadecaneHCID 21713270HCID 21713270, compound

Procedure

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.

Workup

  1. additionrather than a mixture of the 1- and 2-isomers
  2. customThe compound obtained
  3. distillationvacuum distilled
  4. customfurther purified by column chromatography on an alumina column in petroleum ether

Sources & evidence

ORD record
ord-060721eba2a3439bbaf18fb7c1acf0f9
Source dataset
uspto-grants-2001_08
Patent number
US06270653B1

Reaction notes

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