4-Cyanobenzaldehyde → p-Cyanobenzyl alcohol

HRID 1934712Notes

Reaction equation

HRID 1934712 reaction equation
[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[CH:5][CH:4]=1)#[N:2].[BH4-].[Na+]>C(O)C.O1CCCC1>[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH2:7][OH:8])=[CH:5][CH:4]=1)#[N:2]

Participants

5

Reactant 2

HCID 660424-CyanobenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 160549p-Cyanobenzyl alcoholYield 93.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of 4-cyanobenzaldehyde (5.00 g) in ethanol (50 mL) and tetrahydrofuran (20 mL) was added sodium borohydride (2.16 g) under ice-water cooling, and the mixture was stirred for an hour at 0° C. After evaporation of the solvent, the residue was partitioned between ethyl acetate and water. The separated organic layer was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo to give 4-cyanobenzyl alcohol (4.76 g) as a colorless oil.

Workup

  1. customAfter evaporation of the solvent
  2. customthe residue was partitioned between ethyl acetate and water
  3. washThe separated organic layer was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-f9ca8c348cb74a35afd516e14b5e4c60
Source dataset
uspto-grants-2002_05
Patent number
US06384080B1

Reaction notes

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