1-Bromodecane → 2-(4-Pentylphenyl)-6-decyloxyquinoline

HRID 1939116Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1939116
[CH2:1]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[C:17]([OH:22])[CH:18]=3)[N:13]=2)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5].Br[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33].[OH-].[K+]>C(O)CCC>[CH2:1]([C:6]1[CH:7]=[CH:8][C:9]([C:12]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[C:17]([O:22][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH:18]=3)[N:13]=2)=[CH:10][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

Komponenten

5

Edukt 3

HCID 81731-BromodecaneHCID 14797Potassium Hydroxide2×HCID 214668092-(4-Pentylphenyl)quinoline-6-ol

Produkt 1

HCID 214668102-(4-Pentylphenyl)-6-decyloxyquinolineAusbeute 67,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2631-ButanolLösungsmittel2×

Versuchsvorschrift

Then, 0.23 g (0.79 mM) of 2-(4-pentylphenyl)-6-hydroxyquinoline, 0.17 ml (0.82 mM) of 1-bromodecane and 2.6 ml (0.02 g of potassium hydroxide per 1 ml of butanol) of a solution of potassium hydroxide in butanol were placed in a 20 ml-round bottomed flask and refluxed for 2 hours and 50 minutes under stirring. After the reaction, the reaction mixture was left standing overnight in a freezer at -20° C. to precipitate a crystal. The crystal was recovered by filtration and successively washed with methanol and water. The resultant crystal was purified by silica gel column chromatography (eluent: toluene) and recrystallized from a mixture solvent (toluene and methanol) to obtain 0.23 g of 2-(4-pentylphenyl)-6-decyloxyquinoline (Yield: 67.5%).

Aufarbeitung

  1. temperaturerefluxed for 2 hours and 50 minutes
  2. customAfter the reaction
  3. waitthe reaction mixture was left
  4. customto precipitate a crystal
  5. filtrationThe crystal was recovered by filtration
  6. washsuccessively washed with methanol and water
  7. customThe resultant crystal was purified by silica gel column chromatography (eluent: toluene)
  8. customrecrystallized from a mixture solvent (toluene and methanol)

Quellen und Nachweise

ORD-Eintrag
ord-caf55deb589d4305a15cc7d36174655e
Quelldatensatz
uspto-grants-1997_12
Patentnummer
US05695684

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