4-Cyanobenzaldehyde → p-Cyanobenzyl alcohol

HRID 342631Notes

Reaction equation

HRID 342631 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>[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH2:7][OH:8])=[CH:5][CH:4]=1)#[N:2]

Participants

4

Reactant 2

HCID 660424-CyanobenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 160549p-Cyanobenzyl alcoholYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-cyanobenzaldehyde (1.97 g, 15.0 mmol) in 50 mL of ethanol at room temperature was added sodium borohydride (0.57 g, 15.0 mmol). After 4 days, the solution was quenched with saturated ammonoum chloride solution, then poured into EtOAc, washed with sat, NaHCO3 soln. and brine, dried (Na2SO4), filtered, and concentrated in vacuo to provide the product (1.82 g, 92% yield) as a white waxy solid which was sufficiently pure for use in the next step without further purification.

Workup

  1. customthe solution was quenched with saturated ammonoum chloride solution
  2. additionpoured into EtOAc
  3. washwashed
  4. dry with materialand brine, dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3d978d1727c74acba730d46f6939d67c
Source dataset
uspto-grants-1999_01
Patent number
US05859012

Reaction notes

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