Dimethylformamide → 3-[4-(3-Phenylpropoxy)phenyl]propanenitrile

HRID 243816Notes

Reaction equation

HRID 243816 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:11])C#N)=[CH:4][CH:3]=1.[C:12]1([CH2:18][CH2:19][CH2:20]Br)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:28][N:29](C)C=O>C(OCC)C>[C:12]1([CH2:18][CH2:19][CH2:20][O:1][C:2]2[CH:3]=[CH:4][C:5]([CH2:8][CH2:11][C:28]#[N:29])=[CH:6][CH:7]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 12503(3-Bromopropyl)benzeneHCID 895432-(4-Hydroxyphenyl)propanenitrile

Product 1

HCID 666906523-[4-(3-Phenylpropoxy)phenyl]propanenitrile

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 4-hydroxyphenylpropanenitrile (5.25 g) in N,N-dimethyl formamide (40 mL), 3-phenylpropyl bromide (7.1 g) and potassium carbonate (14.79 g) were added, followed by stirring at room temperature for 16 hours. Then, the reaction mixture was diluted with diethyl ether and an organic layer was successively washed with water and brine. After the organic layer was dried, the solvent was concentrated and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1) to give the title compound (8.54 g) having the following physical properties.

Workup

  1. washan organic layer was successively washed with water and brine
  2. customAfter the organic layer was dried
  3. concentrationthe solvent was concentrated
  4. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-0c0423f86d3b4bd38e399e087c5797da
Source dataset
uspto-grants-2014_02
Patent number
US08653305B2

Reaction notes

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