N-bromobutanimide → 4-Phenylbutanal

HRID 1272589Notes

Reaction equation

HRID 1272589 reaction equation
[C:1]([O-:4])(=O)[CH3:2].[Na+].[CH2:6]1[C:11](=O)N(Br)[C:8](=O)[CH2:7]1>CC1(C)N([O])C(C)(C)CCC1.C(OCC)(=O)C>[CH2:8]([CH2:2][CH:1]=[O:4])[CH2:7][C:6]1[CH:11]=[CH:8][CH:7]=[CH:6][CH:11]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 517045Sodium Acetate

Product 1

HCID 290304-PhenylbutanalYield 125.2%

Reagents, catalysts & solvents 2

HCID 2724126TempoCatalystHCID 8857Ethyl AcetateSolvent

Procedure

β-Phenethylalcohol (2.0 g, 16.4 mmol), sodium acetate (2.0 g, 24.6 mmol), TEMPO (26 mg, 0.16 mmol) and ethyl acetate (15 ml) were put in a 50-ml egg plant type flask. The suspension was cooled to less than 10° C. in an ice bath, and thereto was added NBS (3.2 g, 18.0 mmol) divided in two portions. The insoluble materials were filtered off and the filtrate was washed with 5% aqueous sodium bicarbonate solution. The crude product was purified by distillation to give phenethylacetaldehyde (1.67 g, yield 85%).

Workup

  1. temperatureThe suspension was cooled to less than 10° C. in an ice bath
  2. filtrationThe insoluble materials were filtered off
  3. washthe filtrate was washed with 5% aqueous sodium bicarbonate solution
  4. distillationThe crude product was purified by distillation

Sources & evidence

ORD record
ord-ee4a25970ee5428885e084760bce01ae
Source dataset
uspto-grants-2007_04
Patent number
US07208634B2

Reaction notes

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