1-Butanol → HCID 68471813, compound

HRID 1929303Notes

Reaction equation

HRID 1929303 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)([O-])=O.[CH2:16]([OH:20])[CH2:17][CH2:18][CH3:19].C(P(CCCC)CCCC)CCC>O>[CH2:16]([O:20][C:4]1[CH2:9][CH:8]=[C:7]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:6]=[CH:5][N:1]=1)[CH2:17][CH2:18][CH3:19]

Participants

5

Reactant 3

HCID 2631-ButanolHCID 71144-Nitro-1,1'-biphenyl2×HCID 13831Tributylphosphine

Product 1

HCID 68471813HCID 68471813, compoundYield 44.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
-40 °C

Procedure

A 22 Liter reaction flask is equipped with a heating mantle, overhead stirring apparatus, condenser, addition funnel, thermometer probe, and nitrogen inlet/outlet. The flask is purged thoroughly with nitrogen and maintained under nitrogen throughout the reaction. The flask is charged with 4-nitrobiphenyl (1700 g, 8.53 moles) and 1-butanol (3793 g, 51.2 moles). The resulting mixture is heated to reflux to form a clear solution. Tributylphosphine (3500 g, 17.3 moles) is charged to the addition funnel and added dropwise to the hot 4-nitrobiphenyl solution. The temperature is gradually increased as needed to maintain reflux. The reaction is monitored by gas chromatography analysis for completion. The reaction is cooled and water is added (500 mL). The reaction is concentrated to an oil, followed by the addition of petroleum ether (8.0 L). The resulting mixture is cooled to −40° C. and filtered to remove undesired tributylphosphine oxide. The filtrate is concentrated again and petroleum ether (8.0 L) is added. The mixture is cooled and filtered. The resulting filtrate is concentrated to an oil and purified by silica gel chromatography to give the title compound (908 g, 44%).

Workup

  1. customA 22 Liter reaction flask
  2. customis equipped with a heating mantle
  3. additionapparatus, condenser, addition funnel
  4. customThe flask is purged thoroughly with nitrogen
  5. temperaturemaintained under nitrogen throughout the reaction
  6. temperatureThe resulting mixture is heated
  7. temperatureto reflux
  8. customto form a clear solution
  9. temperatureThe temperature is gradually increased
  10. temperatureto maintain
  11. temperaturereflux
  12. temperatureThe reaction is cooled
  13. concentrationThe reaction is concentrated to an oil
  14. additionfollowed by the addition of petroleum ether (8.0 L)
  15. filtrationfiltered
  16. customto remove undesired tributylphosphine oxide
  17. concentrationThe filtrate is concentrated again
  18. additionpetroleum ether (8.0 L) is added
  19. temperatureThe mixture is cooled
  20. filtrationfiltered
  21. concentrationThe resulting filtrate is concentrated to an oil
  22. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-d5d204f74c6b4a7e885f70089cabf4e4
Source dataset
uspto-grants-2012_05
Patent number
US08188069B2

Reaction notes

Loading…