Water → 4-(3-Hydroxypropyl)benzonitrile

HRID 1978400Notes

Reaction equation

HRID 1978400 reaction equation
B.[C:2]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][OH:13])=[CH:6][CH:5]=1)#[N:3].O1CCCC1.C(C1C=CC(CCC(O)=O)=CC=1)#N.O.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[C:2]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][OH:13])=[CH:6][CH:5]=1)#[N:3]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 93617423-(4-Cyanophenyl)-propionic acidHCID 178419156HCID 178419156, compound

Product 1

HCID 110841784-(3-Hydroxypropyl)benzonitrileYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Synthesis of 3-(4-Cyanophenyl)propanol Borane-tetrahydrofuran complex (1.0 M in tetrahydrofuran, 33.0 ml, 33.0 mmol) was added dropwise to a stirred solution of 3-(4-cyanophenyl)propionic acid (4.40 g, 25.1 mmol) in tetrahydrofuran (50 ml) at O{umlaut over (uA)} and the stirring was continued at room temperature for 14 hours. Water (50 ml) and potassium carbonate (10.0 g, 72.4 mmol) was added to the mixture. The mixture was extracted with ethyl acetate and the extract was washed with brine, dried over MgSO4 and concentrated in vacuo to give 3-(4-cyanophenyl)propanol as a yellow oil (3.20 g, 79%).

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washthe extract was washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e7d7197a79e347e38b4bad05a86a56a7
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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