Water → 3-[p-(3-Chloro-2-methylpropionyl)benzyl]pyridine

HRID 569159

Reaktionsgleichung

Reaktionsgleichung von HRID 569159
[Cl-].[Al+3].[Cl-].[Cl-].[Cl:5][CH2:6][CH:7]([CH3:11])[C:8](Cl)=[O:9].Cl.[CH2:13]([C:20]1[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O>C(Cl)Cl>[Cl:5][CH2:6][CH:7]([CH3:11])[C:8]([C:17]1[CH:18]=[CH:19][C:14]([CH2:13][C:20]2[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=2)=[CH:15][CH:16]=1)=[O:9]

Komponenten

6

Edukt 4

HCID 962WaterHCID 6451240Aluminum(III) ChlorideHCID 122105453-Benzylpyridine hydrochlorideHCID 124174873-Chloro-2-methylpropanoyl chloride

Produkt 1

HCID 137455203-[p-(3-Chloro-2-methylpropionyl)benzyl]pyridineAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

In 25 ml of methylene chloride was suspended 13.3 g of anhydrous aluminum chloride, and 7.3 g of 3-chloro-2-methylpropionyl chloride was added to the suspension with ice-cooling, after which 8.2 g of 3-benzylpyridine hydrochloride was added in small portions to the suspension. The resulting mixture was subjected to reaction with ice-cooling for 2 hours and then at room temperature for one hour. The reaction mixture was added in small portions to a mixture of 246 ml of iced water and 49 ml of methylene chloride, and the organic layer was separated, while the aqueous layer was extracted with 40 ml of methylene chloride. The organic layers were combined and then 80 ml of water was added thereto after which the resulting mixture was neutralized with sodium hydrogencarbonate. The organic layer was separated, washed with 50 ml of water, and thereafter dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure, and the residue thus obtained was purified by a column chromatography [Wako Silica Gel C-200, eluant: chloroform:ethyl acetate (1:1 by volume)] to obtain 10.53 g (yield 96.0%) of colorless, oily 3-[p-(3-chloro-2-methylpropionyl)benzyl]pyridine.

Aufarbeitung

  1. additionwas added to the suspension with ice-
  2. temperaturecooling
  3. customThe resulting mixture was subjected to reaction with ice-
  4. temperaturecooling for 2 hours
  5. customthe organic layer was separated, while the aqueous layer
  6. extractionwas extracted with 40 ml of methylene chloride
  7. addition80 ml of water was added
  8. customThe organic layer was separated
  9. washwashed with 50 ml of water
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customThe solvent was removed by distillation under reduced pressure
  12. customthe residue thus obtained
  13. customwas purified by a column chromatography [Wako Silica Gel C-200, eluant: chloroform:ethyl acetate (1:1 by volume)]

Quellen und Nachweise

ORD-Eintrag
ord-ea9c9b96fa55494b8c7410a42db06392
Quelldatensatz
uspto-grants-1988_03
Patentnummer
US04731370

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