8-Hydroxyquinoline → 7-Dodecenyl-8-hydroxyquinoline

HRID 462040

Reaktionsgleichung

Reaktionsgleichung von HRID 462040
[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[OH-].[Na+].[I-].[K+].[CH:16](Cl)=[CH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]>CO>[CH:16]([C:3]1[C:2]([OH:1])=[C:11]2[C:6]([CH:7]=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1)=[CH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Komponenten

6

Edukt 4

HCID 19238-HydroxyquinolineHCID 4875Potassium IodideHCID 14798Sodium HydroxideHCID 1229391-Chlorododec-1-ene

Produkt 1

HCID 537619667-Dodecenyl-8-hydroxyquinoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
230 °C

Versuchsvorschrift

One hundred forty five grams (1.0 mole) 8-hydroxyquinoline, 40 gm. sodium hydroxide, 500 ml. methanol and 5 gm. potassium iodide were combined in a two liter round bottom flask. To this was added 243 gm. dodecenyl chloride (as used in Example I) and the mixture stirred under reflux overnight. The product was filtered, taken up in ether and washed with 500 ml. Claisen's alkali (in five portions). The ether solution was washed several times with water until neutral, dried and the solvent stripped to yield 317.9 gm. of crude product. Of this amount, 310.9 gm. was distilled through a one foot Vigreaux after being heated in the pot to 230° C. and cooled to about 100° C. The fractions coming off at 197°-202° C., 0.7 mm. Hg. (51.1 gm.) and 202°-231° C., 0.8 mm. Hg. (96.8 gm.) consisted almost entirely of 7-dodecenyl-8-hydroxyquinoline.

Aufarbeitung

  1. additionTo this was added 243 gm
  2. temperatureunder reflux overnight
  3. filtrationThe product was filtered
  4. washwashed with 500 ml
  5. washThe ether solution was washed several times with water until neutral,
  6. customdried
  7. customto yield 317.9 gm
  8. distillationwas distilled through a one foot Vigreaux
  9. temperaturecooled to about 100° C
  10. customcoming off at 197°-202° C.
  11. custom(51.1 gm.) and 202°-231° C., 0.8 mm. Hg

Quellen und Nachweise

ORD-Eintrag
ord-dfb092fbf22c43169828ac05181c1d4a
Quelldatensatz
uspto-grants-1977_12
Patentnummer
US04065455

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