Acetonitrile → 4-(3-Hydroxypropoxy)benzonitrile

HRID 2078433Notes

Reaction equation

HRID 2078433 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].C(#N)C.Br[CH2:20][CH2:21][CH2:22][OH:23]>O.C1(C)C=CC=CC=1>[OH:23][CH2:22][CH2:21][CH2:20][O:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanolHCID 130194-Cyanophenol

Product 1

HCID 151263514-(3-Hydroxypropoxy)benzonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
84 °C

Procedure

To a flask was added 4-hydroxybenzonitrile (10 g, 82.7 mmol, 1 eq.) and potassium carbonate (13.60 g, 98.7 mmol, 1.25 eq.). To this mixture was added acetonitrile (80 mL) and then, under stirring, 3-bromo-1-propanol (12.25 g, 86.40 mmol, 1.05 eq.). The reaction mixture was heated at reflux (84° C.) for 5 hours before being allowed to cool to room temperature. Toluene (80 mL) and water (50 mL) were added and the resulting mixture was heated (≈30° C.) until all of the solids had gone into solution. The aqueous layer was separated from the organic layer. The organic layer was retained.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto cool to room temperature
  3. temperaturethe resulting mixture was heated (≈30° C.) until all of the solids
  4. customThe aqueous layer was separated from the organic layer

Sources & evidence

ORD record
ord-45690dad38b44a66bfd5cecb4731050a
Source dataset
uspto-grants-2011_04
Patent number
US07928225B2

Reaction notes

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