Methyl thiocyanate → 4-(4-n-Octylphenyl)-2-cyanophenol

HRID 1074114

Reaktionsgleichung

Reaktionsgleichung von HRID 1074114
[CH2:1]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].CS[C:24]#[N:25].[Cl-].[Al+3].[Cl-].[Cl-].[OH-].[Na+]>ClCCCl>[CH2:1]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[C:17]([C:24]#[N:25])[CH:16]=2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Komponenten

6

Edukt 4

HCID 11168Methyl thiocyanateHCID 14798Sodium HydroxideHCID 6451240Aluminum(III) Chloride2×HCID 140472114'-Octyl-[1,1'-biphenyl]-4-ol

Produkt 1

HCID 189501194-(4-n-Octylphenyl)-2-cyanophenol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a suspension of 4-(4-n-octylphenyl)phenol (2.82 g) in 1,2-dichloroethane (40 ml) is added a 2M borone trichloride - 1,2-dichloroethane solution (6 ml) under ice cooling, and thereto are further added methyl thiocyanate (0.82 ml) and aluminum chloride (1.33 g). The mixture is stirred at room temperature until aluminum chloride is dissolved, and is further stirred at 80° C. for 3 hours. After cooling, 4N aqueous sodium hydroxide solution (33 ml) is added to the reaction mixture, and the mixture is stirred at 75°-80° C. for 30 minutes. After cooling, the reaction mixture is washed with methylene chloride, and the aqueous layer is adjusted to pH 2 with 6N hydrochloric acid and then extracted with ether. The extract is dried and then ether is distilled off under reduced pressure. The crude crystal thus obtained is purified by silica gel column chromatography to give 4-(4-n-octylphenyl)-2-cyanophenol (2.03 g) of the following formula: ##STR32##

Aufarbeitung

  1. additionis added a 2M
  2. dissolutionis dissolved
  3. temperatureAfter cooling
  4. stirringthe mixture is stirred at 75°-80° C. for 30 minutes
  5. temperatureAfter cooling
  6. washthe reaction mixture is washed with methylene chloride
  7. extractionextracted with ether
  8. customThe extract is dried
  9. distillationether is distilled off under reduced pressure
  10. customThe crude crystal thus obtained
  11. customis purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-24bd4c6ffc04482eb60d6a08b7bb6d1a
Quelldatensatz
uspto-grants-1990_11
Patentnummer
US04973425

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