Water → p-Cyanobenzyl alcohol

HRID 635536Notes

Reaction equation

HRID 635536 reaction equation
[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH2:7]N)=[CH:5][CH:4]=1)#[N:2].O.S(=O)(=O)(O)[OH:13].N([O-])=O.[Na+]>C1(C)C=CC=CC=1>[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH2:7][OH:13])=[CH:5][CH:4]=1)#[N:2]

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 826084-(Aminomethyl)benzonitrileHCID 23668193Sodium Nitrite

Product 1

HCID 160549p-Cyanobenzyl alcoholYield 51.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

p-Cyanobenzylamine (13.2 g), water (54 g), and toluene (20 g) were mixed, and the mixture was stirred with cooling with ice. Concentrated sulfuric acid (14.7 g) was added to the mixture. Subsequently, a 20 wt % aqueous solution (44.9 g) of sodium nitrite was added dropwise to the mixture over one hour. The mixture was stirred at the same temperature for four hours. For the subsequent process, the procedure of Example 1 was repeated, to thereby obtain 6.8 g of p-cyanobenzyl alcohol (yield 51%). The purity of the product was 98%.

Workup

  1. temperaturewith cooling with ice
  2. stirringThe mixture was stirred at the same temperature for four hours

Sources & evidence

ORD record
ord-68f085270a6545e8920004f6209cb026
Source dataset
uspto-grants-2001_02
Patent number
US06187945B1

Reaction notes

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