1-Butanol → p-Butoxybenzonitrile

HRID 1742767Notes

Reaction equation

HRID 1742767 reaction equation
[CH2:1]([OH:5])[CH2:2][CH2:3][CH3:4].[Na].Cl[C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=1>O>[CH2:1]([O:5][C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 2631-ButanolHCID 121634-ChlorobenzonitrileHCID 5360545Sodium

Product 1

HCID 138435p-Butoxybenzonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

250 ml of butanol and 15.2 g (0.66 mol) of sodium are heated in a sulfonation flask under a protective-gas atmosphere until the metal has fully reacted. The mixture is cooled, p-chlorobenzonitrile is added in portions, and the reaction mixture is subsequently refluxed for about 16 hours. The cooled mixture is poured into water and extracted with ethyl acetate. The organic phase is then dried using MgSO4 and filtered, and the solvent is evaporated, giving 95% of theory of the title product.

Workup

  1. customhas fully reacted
  2. temperatureThe mixture is cooled
  3. temperaturethe reaction mixture is subsequently refluxed for about 16 hours
  4. extractionextracted with ethyl acetate
  5. customThe organic phase is then dried
  6. filtrationfiltered
  7. customthe solvent is evaporated

Sources & evidence

ORD record
ord-3969926c08c64111b0ff119a4ad05e06
Source dataset
uspto-grants-1994_08
Patent number
US05340701

Reaction notes

Loading…