2,3-Dimethylphenol → Xibenolol

HRID 2198832

Reaktionsgleichung

Reaktionsgleichung von HRID 2198832
[C:1]([N:5]1[CH2:8][CH:7]([OH:9])[CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[C:10]1([OH:18])[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[C:11]=1[CH3:17].[OH-].[Na+]>CCOCC>[CH3:17][C:11]1[C:12]([CH3:16])=[CH:13][CH:14]=[CH:15][C:10]=1[O:18][CH2:6][CH:7]([OH:9])[CH2:8][NH:5][C:1]([CH3:2])([CH3:3])[CH3:4]

Komponenten

5

Edukt 3

HCID 106872,3-DimethylphenolHCID 14798Sodium HydroxideHCID 2879861-tert-Butyl-3-hydroxyazetidine

Produkt 1

HCID 146256Xibenolol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

To a mixture of 6.5 parts of 1-(tert.butyl)-3-azetidinol and 6.7 parts of 2,3-xylenol 0.2 part of sodium hydroxide was added, and the mixture was heated at 160° C. for 24 hours. The reaction mixture was cooled and then dissolved in 100 parts of ether. The solution was washed twice with 50 parts of 2 N-sodium hydroxide aqueous solution and extracted three times with 50 parts of 2 N-hydrochloric acid aqueous solution. The extract was washed with 50 parts of ether and was made alkaline by addition of 2 N-sodium hydroxide aqueous solution. The solution was cooled and agitated to form crystals. The resulting crystals were dried and recrystallized twice from ether to yield 9.2 parts of 1-(2',3'-dimethylphenyloxy)-3-(tert.-butylamino)-2-propanol having a melting point of 57° C.

Aufarbeitung

  1. additionwas added
  2. temperatureThe reaction mixture was cooled
  3. washThe solution was washed twice with 50 parts of 2 N-sodium hydroxide aqueous solution
  4. extractionextracted three times with 50 parts of 2 N-hydrochloric acid aqueous solution
  5. washThe extract was washed with 50 parts of ether
  6. additionby addition of 2 N-sodium hydroxide aqueous solution
  7. temperatureThe solution was cooled
  8. customto form crystals
  9. customThe resulting crystals were dried
  10. customrecrystallized twice from ether

Quellen und Nachweise

ORD-Eintrag
ord-9600be261acb4834855eb3c0ecbd4206
Quelldatensatz
uspto-grants-1982_11
Patentnummer
US04360464

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