Water → p-Cyanobenzyl alcohol

HRID 1243504Notes

Reaction equation

HRID 1243504 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-16f042e5e2904e699a9141fd3f0a38ce
Source dataset
uspto-grants-2006_10
Patent number
US07119098B2

Reaction notes

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