Potassium Carbonate → HCID 23432392, compound

HRID 274150Notes

Reaction equation

HRID 274150 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[Br:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]Br>CC(C)=O>[Br:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 123681,6-DibromohexaneHCID 1406104'-Hydroxy-4-biphenylcarbonitrile

Product 1

HCID 23432392HCID 23432392, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4'-hydroxy-4-cyanobiphenyl (7.8 g, 40 mmol), potassium carbonate (8.3 g, 60 mmol), 1,6-dibromohexane (29.8 g, 120 mmol), and acetone (80 milliliters ("mL")) was heated to reflux for 6 hours ("h") under a nitrogen atmosphere. The acetone was concentrated and the residue dissolved in ether-dichloromethane (4:1, 400 mL). The solution was filtered through glass fiber. The filtrate was washed with water and brine, dried over magnesium sulfate, and concentrated. Excess 1,6-dibromohexane was removed by Kugelrohr distillation up to 75° C. at 0.1 mm Hg. The material remaining in the pot was recrystallized from ethanol (100 mL), filtered while hot, and cooled in the freezer to give crystals of the 4'-(6-bromohexyloxy)-4-cyanobiphenyl (9.6 g, 67%): melting point ("mp") 65.5-66° C., nematic mesophase at 63° C. in cooling; NMR (CDCl3) 7.55(s, 4H), 7.49(d, 2H), 6.82(d, 2H), 3.91(t, 2H), 2.0-1.3(m, 8H); IR (CH2Cl2) 2222, 1602 cm-1.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 6 hours ("h") under a nitrogen atmosphere
  3. concentrationThe acetone was concentrated
  4. dissolutionthe residue dissolved in ether-dichloromethane (4:1, 400 mL)
  5. filtrationThe solution was filtered through glass fiber
  6. washThe filtrate was washed with water and brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated
  9. customExcess 1,6-dibromohexane was removed by Kugelrohr distillation up to 75° C. at 0.1 mm Hg
  10. custompot was recrystallized from ethanol (100 mL)
  11. filtrationfiltered while hot, and
  12. temperaturecooled in the freezer

Sources & evidence

ORD record
ord-b9cade90e085407fb48a6e2560a6d9d1
Source dataset
uspto-grants-1995_02
Patent number
US05389285

Reaction notes

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