1-Bromooctane → 4-n-Octyloxy-4'-acetylbiphenyl

HRID 1762769Notes

Reaction equation

HRID 1762769 reaction equation
[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17](=[O:19])[CH3:18])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)(=O)[CH3:2].[OH-].[K+].Br[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]CC>C(OCCO)C>[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17](=[O:19])[CH3:18])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Participants

5

Reactant 3

HCID 81401-BromooctaneHCID 14797Potassium HydroxideHCID 135310454-Acetoxy-4'-acetylbiphenyl

Product 1

HCID 146697594-n-Octyloxy-4'-acetylbiphenylYield 75.8%

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Procedure

4-Acetyloxy-4'-acetylbiphenyl (80.0 g, 0.315 mol) was suspended in ethylene glycol monoethyl ether (300 ml), followed by heating with stirring to obtain a uniform solution, pouring a 50% aqueous solution of KOH (70 g) therein, heating under reflux for 30 minutes, dropwise adding 1-bromo-n-octane (62.7 g, 0.325 mol), heating under reflux for 5 hours, cooling with air, pouring the solution on ice (1 l), extracting with toluene (2 l), washing the toluene layer with an acid, then with an alkali aqueous solution, further with water till the washing water became neutral, distilling off toluene for solidification, filtering on heating with toluene (1 l) and active carbon, and recrystallizing to obtain 4-n-octyloxy-4'-acetylbiphenyl (77.5 g). Yield: 75.71%. This product exhibited a smectic B liquid crystal phase (SB), and its C-SB point and SB-I point were 92.5° C. and 132.9° C., respectively.

Workup

  1. temperatureby heating
  2. customto obtain a uniform solution
  3. temperatureheating
  4. temperatureunder reflux for 30 minutes
  5. temperatureunder reflux for 5 hours
  6. temperaturecooling with air
  7. additionpouring the solution on ice (1 l)
  8. extractionextracting with toluene (2 l)
  9. washwashing the toluene layer with an acid
  10. distillationdistilling off toluene for solidification
  11. filtrationfiltering
  12. temperatureon heating with toluene (1 l) and active carbon
  13. customrecrystallizing

Sources & evidence

ORD record
ord-d72f474d51944fc38d22bfec86b19478
Source dataset
uspto-grants-1989_05
Patent number
US04834907

Reaction notes

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