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

HRID 1492351

Reaktionsgleichung

Reaktionsgleichung von HRID 1492351
[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].B(Cl)(Cl)Cl.CS[C:28]#[N:29].[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:28]#[N:29])[CH:16]=2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Komponenten

7

Edukt 5

HCID 11168Methyl thiocyanateHCID 14798Sodium HydroxideHCID 25135Boron TrichlorideHCID 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-DichloroethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a suspension of 2.82 g of 4-(4-n-octylphenyl) phenol in 40 ml of 1,2-dichloroethane were added under ice cooling, 6 ml of a solution of boron trichloride (2M) in 1,2-dichloroethane, and then 0.82 ml of methyl thiocyanate and 1.33 g of aluminum chloride. The mixture was stirred at room temperature until the aluminum chloride is dissolved, further stirred for 3 hours at 80° C. and cooled to room temperature. To the resulting mixture was added further 33 ml of 4N-sodium hydroxide solution. The mixture was stirred for 30 minutes at 75° to 80° C. After cooling, the reaction mixture was washed with methylene chloride. The aqueous phase was adjusted to pH2 with 6N hydrochloric acid and extracted with ether. The extract was dried and evaporated under reduced pressure to obtain crude crystals. The crystals were purified by a silica gel column chromatography to give 2.03 g of 4-(4-n-octylphenyl)-2-cyanophenol.

Aufarbeitung

  1. additionwere added under ice cooling
  2. dissolutionis dissolved
  3. temperaturecooled to room temperature
  4. stirringThe mixture was stirred for 30 minutes at 75° to 80° C
  5. temperatureAfter cooling
  6. washthe reaction mixture was washed with methylene chloride
  7. extractionextracted with ether
  8. customThe extract was dried
  9. customevaporated under reduced pressure
  10. customto obtain crude crystals
  11. customThe crystals were purified by a silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-a6811cdea89441968ceecba62e61f17d
Quelldatensatz
uspto-grants-1994_12
Patentnummer
US05374373

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