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

HRID 1732242Notes

Reaction equation

HRID 1732242 reaction equation
[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

Participants

4

Reactant 3

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

Product 1

HCID 545213892,6-Dimethyl-4-propoxyazobenzeneYield 93.1%

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-405be79c032c421a82922b9932996313
Source dataset
uspto-grants-1980_12
Patent number
US04237068

Reaction notes

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