Toluene → 2,3,5-Trimethylpyridine

HRID 35466

Reaktionsgleichung

Reaktionsgleichung von HRID 35466
C[Li].[N:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH3:10])[CH:4]=1.[C:11]1(C)C=CC=CC=1>CCOCC>[N:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH3:10])[C:4]=1[CH3:11]

Komponenten

5

Edukt 3

HCID 1140TolueneHCID 115653,5-DimethylpyridineHCID 178418348HCID 178418348, Verbindung

Produkt 1

HCID 127592,3,5-Trimethylpyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

To 500 ml of a 5% solution of methyl lithium in ether are added dropwise at room temperature under argon 1200 ml of ether, subsequently 35.6 g of 3,5-lutidine (3,5-dimethylpyridine) and subsequently 400 ml of toluene. The ether is distilled off completely, whereupon the solution is stirred at 100° for 4 hours. Ice is then added portionwise thereto while cooling with methanol/ice until evolution of heat no longer occurs. The toluene phase is separated from precipitated solid and extracted with 66 ml of semi-concentrated hydrochloric acid. The separated aqueous phase is adjusted to a pH of about 10 with 3N sodium hydroxide solution while cooling and extracted twice with 300 ml of ether. The ether extracts are dried over sodium sulphate and evaporated. The residue is distilled in vacuo at 20 mm/72°-74°; there is obtained 2,3,5-collidine (2,3,5-trimethylpyridine) which has a purity of 99.15% according to gas chromatography.

Aufarbeitung

  1. distillationThe ether is distilled off completely
  2. additionIce is then added portionwise
  3. temperaturewhile cooling with methanol/ice until evolution
  4. temperatureof heat no longer
  5. customThe toluene phase is separated
  6. customfrom precipitated solid
  7. extractionextracted with 66 ml of semi-concentrated hydrochloric acid
  8. temperaturewhile cooling
  9. extractionextracted twice with 300 ml of ether
  10. dry with materialThe ether extracts are dried over sodium sulphate
  11. customevaporated
  12. distillationThe residue is distilled in vacuo at 20 mm/72°-74°

Quellen und Nachweise

ORD-Eintrag
ord-1903b180db0b404787d762335751ae50
Quelldatensatz
uspto-grants-1988_08
Patentnummer
US04766133

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