Hydrochloric Acid → 4-Benzhydrylpyridine

HRID 1193636

Reaktionsgleichung

Reaktionsgleichung von HRID 1193636
[C:1]1([C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.I.[OH-].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(O)(=O)C>[C:1]1([CH:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]2[CH:10]=[CH:11][N:12]=[CH:13][CH:14]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24477Sodium ThiosulfateHCID 24841Hydrogen iodideHCID 74177alpha,alpha-Diphenyl-4-pyridinemethanol

Produkt 1

HCID 772524-Benzhydrylpyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A mixture of 99 g (0.379 mole) of diphenyl-4-pyridyl-methanol, 50 ml of conc. hydrochloric acid, 200 ml of 57% hydroiodic acid and 200 ml of glacial acetic acid was refluxed for 41/2 hr and then was stirred at room temperature for 12 hr. The reaction mixture was poured over ice and was made basic with 50% sodium hydroxide. An aqueous solution of sodium thiosulfate was added, and the mixture was extracted with methylene chloride. The methylene chloride solution was dried over magnesium sulfate and the solvent was removed in vacuo. The residue was recrystallized from a mixture of methylene chloride-ether-hexane to give two crops of crystalline solids: Crop I, 40.87 g (44.0%), m.p. 124-126; Crop II, 25.38 g (27.3%), m.p. 123-125. Analysis of the mixture of the Crops I and II was as follows:

Aufarbeitung

  1. temperaturewas refluxed for 41/2 hr
  2. additionThe reaction mixture was poured over ice
  3. extractionthe mixture was extracted with methylene chloride
  4. dry with materialThe methylene chloride solution was dried over magnesium sulfate
  5. customthe solvent was removed in vacuo
  6. customThe residue was recrystallized from a mixture of methylene chloride-ether-hexane
  7. customto give two crops of crystalline solids

Quellen und Nachweise

ORD-Eintrag
ord-f0394fceb32449ae8535dcd4e97b96bd
Quelldatensatz
uspto-grants-1989_03
Patentnummer
US04810713

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