3-Chloro-1-propanol → HCID 13796792, compound

HRID 1377895Notes

Reaction equation

HRID 1377895 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)#[N:2].[OH-].[Na+].Cl[CH2:19][CH2:20][CH2:21][OH:22]>C(O)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:19][CH2:20][CH2:21][OH:22])=[CH:11][CH:10]=2)=[CH:7][CH:8]=1)#[N:2]

Participants

5

Reactant 3

HCID 123133-Chloro-1-propanolHCID 14798Sodium Hydroxide2×HCID 1406104'-Hydroxy-4-biphenylcarbonitrile

Product 1

HCID 13796792HCID 13796792, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

Into a 300 ml flask, 20 g (102.4 mmol) of 4-cyano-4'-hydroxybiphenyl, 140 ml of ethanol and a NaOH aqueous solution (7.48 g (132.2 mmol) of NaOH/40 ml of water) were added. The mixture was stirred at 80° C. for 10 minutes, and then 10.66 g (112.8 mmol) of 3-chloro-1-propanol was added thereto. The mixture was heated and refluxed for 18 hours. Ethanol was distilled off. Then, 300 ml of water was added to the reaction solution, and the mixture was neutralized with hydrochloric acid. Precipitated crystals were collected by filtration. Then, 1200 ml of toluene was added thereto, and the toluene layer was washed with water and a saturated sodium chloride aqueous solution and then dried over anhydrous sodium sulfate. Further, the solvent was distilled off under reduced pressure, and the residue was recrystallized from ethanol to obtain 5.34 g (yield: 21%) of 4-cyano-4'-(3-hydroxypropoxy)biphenyl (7) as colorless crystals.

Workup

  1. temperatureThe mixture was heated
  2. temperaturerefluxed for 18 hours
  3. distillationEthanol was distilled off
  4. additionThen, 300 ml of water was added to the reaction solution
  5. customPrecipitated crystals
  6. filtrationwere collected by filtration
  7. additionThen, 1200 ml of toluene was added
  8. washthe toluene layer was washed with water
  9. dry with materiala saturated sodium chloride aqueous solution and then dried over anhydrous sodium sulfate
  10. distillationFurther, the solvent was distilled off under reduced pressure
  11. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-e397c68027954a708c7201055ddc8add
Source dataset
uspto-grants-1997_09
Patent number
US05665856

Reaction notes

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