2-Methylpyridine → 2-Methyl-1-(8-phenyl-octyl)-pyridinium bromide

HRID 84316

Reaktionsgleichung

Reaktionsgleichung von HRID 84316
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[N:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH3:22]>C(#N)C>[Br-:1].[CH3:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][N+:16]=1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Komponenten

4

Edukt 2

HCID 79752-MethylpyridineHCID 563758(8-Bromooctyl)benzene

Produkt 1

HCID 247811032-Methyl-1-(8-phenyl-octyl)-pyridinium bromideAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

(8-Bromo-octyl)-benzene (1 mmol) was added to a solution of 2-picoline (3 mmol) in acetonitrile, and the solution mixture was refluxed for 24 hours. The acetonitrile was removed in a vacuum, and the resulting residue was partitioned between ether and water. The aqueous layer was washed extensively with ether until no picoline was left in the aqueous layer. The resulting aqueous solution of the product was extracted with chloroform. The chloroform was removed to afford the product (70%). 1HNMR (300 MHz, CDCl3, ppm) 9.74 (d, 1H), 8.35 (m, 1H), 7.96 (m, 1H), 7.86 (d, 1H), 7.15-7.25 (m, 4H), 4.92 (t, 2H), 2.95 (s, 3H), 1.88-1.98 (m, 2H), 1.54-1.64 (m, 2H), 1.39-1.49 (m, 2H), 1.25-1.38 (br, 6H).

Aufarbeitung

  1. temperaturethe solution mixture was refluxed for 24 hours
  2. customThe acetonitrile was removed in a vacuum
  3. customthe resulting residue was partitioned between ether and water
  4. washThe aqueous layer was washed extensively with ether until no picoline
  5. waitwas left in the aqueous layer
  6. extractionThe resulting aqueous solution of the product was extracted with chloroform
  7. customThe chloroform was removed

Quellen und Nachweise

ORD-Eintrag
ord-d1042ef966c84333b9177bb4e2025e7a
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846937B2

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