1-Bromopropane → 3-propoxybenzonitrile

HRID 1666903Notes

Reaction equation

HRID 1666903 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].[CH3:10][CH2:11][CH2:12]Br.C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH2:10]([O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6])[CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 78401-BromopropaneHCID 11430Potassium CarbonateHCID 133943-Cyanophenol

Product 1

HCID 186762233-propoxybenzonitrile

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

Combine 3-hydroxybenzonitrile (11.052 gm; 92.8 mmol), n-propyl bromide (24.4 gm; 198 mmol), and potassium carbonate (38.65 gm; 280 mmol) in 2-butanone (175 mL) and heat and reflux. After 17 h., cool the mixture to room temperature, and decant the solution and concentrate by rotary evaporation. Partition the residue between diethyl ether (150 mL) and water (150 mL), separate the layers and extract the aqueous layer with diethyl ether (2×100 mL). Combine the organic layers and wash with water, 1 N NaOH, and water, dry over MgSO4, and concentrate. Distill the residue to give the title compound.

Workup

  1. temperaturereflux
  2. customdecant the solution
  3. concentrationconcentrate by rotary evaporation
  4. customPartition the residue between diethyl ether (150 mL) and water (150 mL)
  5. customseparate the layers
  6. extractionextract the aqueous layer with diethyl ether (2×100 mL)
  7. washCombine the organic layers and wash with water, 1 N NaOH, and water
  8. dry with materialdry over MgSO4
  9. concentrationconcentrate
  10. distillationDistill the residue

Sources & evidence

ORD record
ord-25337728a66d4919b763a10e1179fbd7
Source dataset
uspto-grants-2011_10
Patent number
US08044090B2

Reaction notes

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