Water → p-Cyanobenzyl alcohol

HRID 585541Notes

Reaction equation

HRID 585541 reaction equation
[CH:1]([C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1)=[O:2].[BH4-].[Na+].O>CO>[OH:2][CH2:1][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 660424-CyanobenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 160549p-Cyanobenzyl alcohol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
5 °C

Procedure

A stirred suspension of 4-formylbenzonitrile (10.0 g; 0.0763 moles) in methanol (100 mL) under nitrogen was cooled to 5° C. Sodium borohydride (1.45 g; 0.0382 moles) was added. After 30 minutes the mixture was added to water (300 mL) and extracted with ethyl acetate (4×100 mL). The combined extracts were washed with aqueous sodium chloride solution (50 mL) and dried over sodium sulfate. Following filtration and removal of solvent under vacuum the product, 4-(hydroxymethyl)benzonitrile, (9.44 g; 93%) was obtained as a white solid. 1H NMR (400 MHz) CDCl3 δ 7.61-7.66 (2H, m), 7.45-7.50 (2H, m), 4.78 (2H, d, J=5.5 Hz), 2.27 (1H, t, J=5.5 Hz).

Workup

  1. extractionextracted with ethyl acetate (4×100 mL)
  2. washThe combined extracts were washed with aqueous sodium chloride solution (50 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltration and removal of solvent under vacuum the product, 4-(hydroxymethyl)benzonitrile
  5. custom(9.44 g; 93%) was obtained as a white solid

Sources & evidence

ORD record
ord-af826429149f4024a78e543e01d4030b
Source dataset
uspto-grants-2005_08
Patent number
US06933304B2

Reaction notes

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