Acetaldehyde → 4-Azidocinnamaldehyde

HRID 1885048Notes

Reaction equation

HRID 1885048 reaction equation
[N:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][CH:5]=1)=[N+:2]=[N-:3].[OH-].[Na+].[CH:14](=[O:16])[CH3:15]>C(O)(C)C.O>[N:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[CH:15][CH:14]=[O:16])=[CH:6][CH:5]=1)=[N+:2]=[N-:3]

Participants

6

Reactant 3

HCID 177Acetaldehyde3×HCID 14798Sodium HydroxideHCID 903854-Azidobenzaldehyde

Product 1

HCID 446298674-AzidocinnamaldehydeYield 28%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 3776IsopropanolSolvent

Procedure

4-Azidobenzaldehyde (14.71 g, 0.1 mol) was dissolved in a solvent mixture of isopropyl alcohol (50 g) and pure water (15 g). Under cooling in an ice bath, sodium hydroxide (1 g) dissolved in pure water (10 g) was added to the solution, and the resultant mixture was stirred for ten minutes. Acetaldehyde (4.41 g, 0.1 mol) was added to the mixture, and the resultant mixture was stirred for two hours at the same temperature. Subsequently, acetaldehyde (4.41 g, 0.1 mol) was again added to the mixture, and the resultant mixture was stirred for a further three hours. The formed precipitates were collected through filtration and dried, to thereby yield 4.82 g of p-azido-cinnamaldehyde as brown solid (yield: 28%) as a mixture containing acetaldehyde (2.7%).

Workup

  1. temperatureUnder cooling in an ice bath
  2. additionwas added to the solution
  3. customThe formed precipitates
  4. filtrationwere collected through filtration
  5. customdried

Sources & evidence

ORD record
ord-21c609526a4543118aefaab5df69aa5c
Source dataset
uspto-grants-2004_07
Patent number
US06768027B2

Reaction notes

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