3-Bromo-1-propanol → 3-(4'-Cyano-4-biphenylyl)-1-propanol

HRID 652703Notes

Reaction equation

HRID 652703 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12](O)=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)#[N:2].Br[CH2:17][CH2:18][CH2:19][OH:20].[OH-].[Na+]>C(O)C.O>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([CH2:17][CH2:18][CH2:19][OH:20])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)#[N:2]

Participants

6

Reactant 3

HCID 123083-Bromo-1-propanolHCID 14798Sodium HydroxideHCID 1406104'-Hydroxy-4-biphenylcarbonitrile

Product 1

HCID 201962263-(4'-Cyano-4-biphenylyl)-1-propanol

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

4'-Cyano-4-hydroxybiphenyl (6 g, 0.02 mol) and 3-bromo-1-propanol (5.6 g, 0.04 mol) were dissolved in ethanol (300 ml), followed by gradually dropwise adding an aqueous solution of sodium hydroxide (10 g) in water (20 ml) over 30 minutes, continuing, as it was, stirring for 40 hours, thereafter distilling off ethanol (about 200 ml) under reduced pressure, then adding water (500 ml), extracting the resulting deposited crystals three times with toluene (100 ml), removing insoluble matter by filtration, washing the toluene layer twice with a 2N aqueous solution of NaOH, further 3 times with water, drying over anhydrous sodium sulfate, completely distilling off toluene and recrystallizing the residual crystals from methanol to prepare 3-(4'-cyano-4-biphenylyl)-1-propanol. Yield: 2 g (28%). This product exhibited liquid crystal phases and its C-N point was 109.0°~110.7° C. and its N-I point was 113.6° C.

Workup

  1. distillationdistilling off ethanol (about 200 ml) under reduced pressure
  2. extractionadding water (500 ml), extracting the resulting
  3. customremoving insoluble matter
  4. filtrationby filtration
  5. washwashing the toluene layer twice with a 2N aqueous solution of NaOH, further 3 times with water
  6. dry with materialdrying over anhydrous sodium sulfate
  7. distillationcompletely distilling off toluene
  8. customrecrystallizing the residual crystals from methanol
  9. customto prepare 3-(4'-cyano-4-biphenylyl)-1-propanol
  10. customwas 109.0°~110.7° C.
  11. customwas 113.6° C.

Sources & evidence

ORD record
ord-4cd419b6dfa44d449fffce427c78cd15
Source dataset
uspto-grants-1987_06
Patent number
US04673529

Reaction notes

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