Potassium Carbonate → 4-((5-Chloropentyl)oxy)benzonitrile

HRID 2209724Notes

Reaction equation

HRID 2209724 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1)#[N:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][Cl:22]>C(#N)C>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([O:9][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][Cl:22])=[CH:5][CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 130194-CyanophenolHCID 960701-Bromo-5-chloropentane

Product 1

HCID 193815104-((5-Chloropentyl)oxy)benzonitrile

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A stirred solution of 4-cyanophenol (80.9 g, 0.679 mol) in 1260 mL of acetonitile is treated with potassium carbonate (93.9 g, 0.679 tool) and 1-bromo-5-chloropentane (126 g, 0.679 mmol). The reaction is refluxed overnight and potassium carbonate is filtered off. The filtrate is concentrated in vacuo to generate oil which is partitioned between ether and water. The organic layer is washed with water, dried with magnesium sulfate, and concentrated in vacuo to afford 5-(4-cyanophenoxy)pentyl chloride as a white solid.

Workup

  1. temperatureThe reaction is refluxed overnight
  2. filtrationpotassium carbonate is filtered off
  3. concentrationThe filtrate is concentrated in vacuo
  4. customis partitioned between ether and water
  5. washThe organic layer is washed with water
  6. dry with materialdried with magnesium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9d6083dff4c84088802aec3f23a9da66
Source dataset
uspto-grants-1995_10
Patent number
US05455274

Reaction notes

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