Ethanol → 4-Cyanobenzaldehyde oxime

HRID 1457715Notes

Reaction equation

HRID 1457715 reaction equation
[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1)#[N:2].CCO.Cl.[NH2:15][OH:16]>N1C=CC=CC=1>[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[N:15][OH:16])=[CH:5][CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 660424-Cyanobenzaldehyde2×HCID 443297Hydroxyamine hydrochloride

Product 1

HCID 52147424-Cyanobenzaldehyde oximeYield 100%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

This material was prepared from 4-cyanobenzaldehyde according to Kawase and Kikugawa (J. Chem. Soc., Perkin Trans I 1979, 643). To a solution of 4-cyanobenzaldehyde (1.31 g, 10 mmol) in 1:1 EtOH:pyridine (10 mL) was added hydroxylamine hydrochloride (0.70 g, 10 mmol). The resulting solution was stirred at room temperature for 18 h and was concentrated in vacuo to one-half volume. To this solution was added ice water, causing the product to crystallize from solution. Recrystallization from EtOH--water followed by drying over P2O5 afforded 1.46 g (100%) of the desired oxime; mp: 167.8°-169.4° C.

Workup

  1. concentrationwas concentrated in vacuo to one-half volume
  2. additionTo this solution was added ice water
  3. customto crystallize from solution
  4. customRecrystallization from EtOH
  5. dry with materialby drying over P2O5

Sources & evidence

ORD record
ord-a999af3dbca64eac8520782e08014c18
Source dataset
uspto-grants-1998_12
Patent number
US05849736

Reaction notes

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