Water → 4-(Octyloxy)-N,N-diphenylaniline

HRID 338040Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 338040
[C:1]1([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C2[C:18](=[CH:19][CH:20]=[C:21]3[C:26]=2N=CC=C3)[CH:17]=[CH:16][CH:15]=1.[OH2:28].[OH-].[K+].[C:31]1(C)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>>[CH2:15]([O:28][C:11]1[CH:10]=[CH:9][C:8]([N:7]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:13][CH:12]=1)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:26]

Komponenten

6

Edukt 5

HCID 962WaterHCID 1140TolueneHCID 13181,10-PhenanthrolineHCID 11487DiphenylamineHCID 14797Potassium Hydroxide

Produkt 1

HCID 189967534-(Octyloxy)-N,N-diphenylanilineAusbeute 65 %

Versuchsvorschrift

Adding diphenylamine (3.36 g, 20 mmol), 1-iodine-4-octyloxy benzene (18.9 g, 98.4 mmol), phenanthroline.H2O (0.2 g), cuprous chloride (0.2 g) and potassium hydroxide (3.36 g, 60 mmol) into toluene (50 mL), mixing at temperature of 100° C. Refluxing for 36 hours and cooling to room temperature, evaporation to eliminate solvent, washing by dilute hydrochloric acid and water for three times, then chloroform extraction. After that, combining organic phase and washing by diluted NaCl solution and water for two times, and then drying by anhydrous magnesium sulfate and filtering, evaporating the solvent, using petroleum ether/dichloromethane (8:1, v/v) as eluent to elutriate the remainder, separating by silica gel column chromatography to obtain a colorless oily liquid, the yield was 65%.

Aufarbeitung

  1. temperatureRefluxing for 36 hours
  2. customevaporation
  3. washwashing by dilute hydrochloric acid and water for three times
  4. extractionchloroform extraction
  5. washwashing by diluted NaCl solution and water for two times
  6. dry with materialdrying by anhydrous magnesium sulfate
  7. filtrationfiltering
  8. customevaporating the solvent
  9. customseparating by silica gel column chromatography
  10. customto obtain a colorless oily liquid

Quellen und Nachweise

ORD-Eintrag
ord-4664656a50ac4967af523c2b33fbee88
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889825B2

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