1-Bromopropane → 2,6-Dimethyl-4-propoxyazobenzene

HRID 1856294Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1856294
[Na].[CH3:2][C:3]1[CH:8]=[C:7]([OH:9])[CH:6]=[C:5]([CH3:10])[C:4]=1[N:11]=[N:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.Br[CH2:20][CH2:21][CH3:22]>>[CH3:2][C:3]1[CH:8]=[C:7]([O:9][CH2:20][CH2:21][CH3:22])[CH:6]=[C:5]([CH3:10])[C:4]=1[N:11]=[N:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Komponenten

4

Edukt 3

HCID 78401-BromopropaneHCID 33198223,5-Dimethyl-4-(phenyldiazenyl)phenolHCID 5360545Sodium

Produkt 1

HCID 545213892,6-Dimethyl-4-propoxyazobenzeneAusbeute 93,1 %

Versuchsvorschrift

To a solution of sodium (2.0 g) in absolute alcohol (120 ml) was added 2,6-dimethyl-4-hydroxyazobenzene (18.3 g) and 1-bromo propane (20 g). The mixture was refluxed for three hours and was left overnight at room temperature. A precipitate of sodium bromide was filtered off, was washed with some cold absolute ethanol, and was discarded. The alcohol was removed from the filtrate by distillation, the residue was dissolved in ether (200 ml), and was extracted with 2% sodium hydroxide solution (4×50 ml) and once with water. After drying (Na2SO4) and filtering, the ether solution was evaporated to dryness leaving a residual oily material (20.2 g), sufficiently pure for the following reaction step.

Aufarbeitung

  1. temperatureThe mixture was refluxed for three hours
  2. filtrationA precipitate of sodium bromide was filtered off
  3. washwas washed with some cold absolute ethanol
  4. customThe alcohol was removed from the filtrate by distillation
  5. dissolutionthe residue was dissolved in ether (200 ml)
  6. extractionwas extracted with 2% sodium hydroxide solution (4×50 ml) and once with water
  7. dry with materialAfter drying (Na2SO4)
  8. filtrationfiltering
  9. customthe ether solution was evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-cc7f7a2cc4c9400fae9171e35472b43b
Quelldatensatz
uspto-grants-1980_08
Patentnummer
US04218477

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