4-Hydroxyazobenzene → HCID 86761961, compound

HRID 454783Notes

Reaction equation

HRID 454783 reaction equation
[C:1]1([N:7]=[N:8][C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(C)([O-])C.[K+].Br[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH:32]=[CH2:33]>O>[CH2:33]([O:15][C:12]1[CH:13]=[CH:14][C:9]([N:8]=[N:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:10][CH:11]=1)[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH:24]=[CH2:23]

Participants

5

Reactant 3

HCID 155294-HydroxyazobenzeneHCID 28414811-Bromo-1-undeceneHCID 23665647Potassium tert-butoxide

Product 1

HCID 86761961HCID 86761961, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-(phenyldiazenyl)phenol (2.100 g; 10.60 mmol) and potassium tert-butoxide (1.247 g; 11.13 mmol) were placed in a dry, two-neck, round-bottom flask equipped with a magnetic stirring bar, a reflux condenser, and a rubber septum. The flask was evacuated and purged with dry argon, then 25 mL of anhydrous N,N-dimethylformamide was added while stirring. As soon as the solids disappeared, 11-bromo-1-undecene (2.44 mL; 2.595 g; 11.13 mmol) was added and the solution was quickly heated, and allowed to reflux for 10 min. Formation of white precipitate was observed, and the color of the solution changed from deep red to bright orange. After 10 min, the heating was discontinued, and the flask was allowed to cool down. The reaction mixture was poured into a separatory funnel containing 100 mL of water, and extracted with four 50 mL portions of hexane. Hexane fractions were combined and dried over magnesium sulfate. Hexane was removed on a rotary evaporator, and the residue was purified by column chromatography (ethyl acetate:hexane 1:20) to give 2.95 g (79.5%) of analytically pure product.

Workup

  1. customequipped with a magnetic stirring bar, a reflux condenser
  2. customThe flask was evacuated
  3. custompurged with dry argon
  4. addition25 mL of anhydrous N,N-dimethylformamide was added
  5. temperaturethe solution was quickly heated
  6. temperatureto reflux for 10 min
  7. temperatureto cool down
  8. additionThe reaction mixture was poured into a separatory funnel
  9. extractionextracted with four 50 mL portions of hexane
  10. dry with materialdried over magnesium sulfate
  11. customHexane was removed on a rotary evaporator
  12. customthe residue was purified by column chromatography (ethyl acetate:hexane 1:20)
  13. customto give 2.95 g (79.5%) of analytically pure product

Sources & evidence

ORD record
ord-23484799950c4eb89d602d2880f5ee79
Source dataset
uspto-grants-2013_07
Patent number
US08496323B2

Reaction notes

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